Skip to main content
SpringerLink
Log in

Water as Solvent in Organic Synthesis

  • Chapter
  • First Online:
Modern Solvents in Organic Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 206))

Abstract

Organic reactions using water as solvent are reviewed with a focus on pericyclic reactions, carbonyl additions, stoichiometric organometallic reactions, oxidations and reductions which show an unusual outcome in terms of reactivity and selectivity compared with those performed in organic solvent. The advantages of using water as a solvent are discussed and related to the hydrophobic effects and the hydrogen-bonding ability of water with a special emphasis on its very high cohesive energy density which strongly favors organic reactions having a negative activation volume.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 16.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Rideout DC, Breslow R (1980) J Am Chem Soc 102:7816

    Article  CAS  Google Scholar 

  2. Grieco PA (1991) Aldrichimica Acta 24:59; Li CJ (1993) Chem Rev 93:2023; Lubineau A, Augé J, Queneau Y (1994) Synthesis 741

    CAS  Google Scholar 

  3. Lubineau A, Queneau Y (1989) Tetrahedron 45:6697

    Article  CAS  Google Scholar 

  4. Grieco PA, Garner P, He ZM (1983) Tetrahedron Lett 24:1897

    Article  CAS  Google Scholar 

  5. Kuntz EG (1987) Chemtech 17:570; Sinou D (1986) Bull Soc Chim Fr 480

    CAS  Google Scholar 

  6. Smithrud DB, Sanford EM, Chao I, Ferguson SB, Carcanague DR, Evanseck JD, Houk KN, Diederich F (1990) Pure Appl Chem 62:2227

    Article  CAS  Google Scholar 

  7. Francks F (1975) In: Water, a comprehensive treatise. Plenum Press, New York, vol 4, p 1

    Google Scholar 

  8. Blokzijl W, Engberts JBFN (1993) Angew Chem Int Ed Engl 32:1545

    Article  Google Scholar 

  9. Frank HS, Evans MW (1945) J Chem Phys 13:507

    Article  CAS  Google Scholar 

  10. Nemethy G, Scheraga HA (1962) J Chem Phys 36:3401

    Article  CAS  Google Scholar 

  11. Ben-Naim A (1965) J Chem Phys 69:3240

    Article  CAS  Google Scholar 

  12. Bernal JD (1964) Proc R Soc London Soc A 280:299

    CAS  Google Scholar 

  13. Stanley HE, Teixera J (1980) J Chem Phys 73:3404

    Article  CAS  Google Scholar 

  14. Davidson DW (1973) In: Water, a comprehensive treatise, Plenum Press, New York, vol 2, p 115

    Google Scholar 

  15. a)_Matubayasi N (1994) J Am Chem Soc 116:1450

    Article  CAS  Google Scholar 

  16. b)_Hecht D, Tadesse L, Walters L (1992) J Am Chem Soc 114:4336

    Article  CAS  Google Scholar 

  17. a)_Privalov PL, Gill SJ (1989) Pure Appl Chem 61:1097

    Article  CAS  Google Scholar 

  18. b)_Dill KA (1990) Biochemistry 29:7133; Muller N (1990) Acc Chem Res 23:23

    Article  CAS  Google Scholar 

  19. Graziano G, Barone G (1996) J Am Chem Soc 118:1831

    Article  CAS  Google Scholar 

  20. Sharp KA, Madan B (1997) J Phys Chem B 101:4343

    Article  CAS  Google Scholar 

  21. Tanford CH (1979) Proc Natl Acad Sci USA 76:4175

    Article  CAS  Google Scholar 

  22. Kauzmann W (1987) Nature 325:763

    Article  Google Scholar 

  23. a) Siskin M, Katritzky AR (1991) Science 254:231

    Article  CAS  Google Scholar 

  24. b) Katritzky AR, Allin SM, Siskin M (1996) Acc Chem Res 29:399

    Article  CAS  Google Scholar 

  25. Dack MRJ (1975) Chem Soc Rev 4:211

    Article  CAS  Google Scholar 

  26. Reichardt C (1988) Solvents and solvent effects in organic chemistry, VCH, Weinheim

    Google Scholar 

  27. Dack MRJ (1974) J Chem Ed 51:231

    Article  CAS  Google Scholar 

  28. Lubineau A (1986) J Org Chem 51:2142

    Article  CAS  Google Scholar 

  29. a)_Blake JF, Lim D, Jorgensen WL (1994) J Org Chem 59:803

    Article  CAS  Google Scholar 

  30. b) Furlani TR, Gao J (1996) J Org Chem 61:5492

    Article  CAS  Google Scholar 

  31. Otto S, Bertoncin F, Engberts JBFN (1996) J Am Chem Soc 118:7702

    Article  CAS  Google Scholar 

  32. Isaacs NS, Maksimovic L, Laila A (1994) J Chem Soc Perkin Trans 2 495

    Google Scholar 

  33. Diels O, Alder K (1931) Ann Chem 490:243

    Google Scholar 

  34. Hopff H, Rantenstrauch CW (1942) Chem Abstr 36:1046

    Google Scholar 

  35. Breslow R (1991) Acc Chem Res 24:159 and Ref 1

    Article  CAS  Google Scholar 

  36. Breslow R (1994) Hydrophobic and antihydrophobic effects on organic reactions in aqueous solution. In: Cramer CJ, Truhlar DG (eds) Structure and reactivity in aqueous solution. ACS Symposium Series 568:291

    Google Scholar 

  37. Blokzijl W, Blandamer MJ, Engberts JBFN (1991) J Am Chem Soc 113:4241

    Article  CAS  Google Scholar 

  38. Schneider H-J, Sangwan NK (1986) J Chem Soc Chem Commun 1787

    Google Scholar 

  39. a) Sangwan NK, Schneider H-J (1989) J Chem Soc Perkin Trans 2 1223

    Google Scholar 

  40. b) Cativiela C, Garcia JI, Gil J, Martinez RM, Mayoral JA, Salvatella L, Urieta JS, Mainar AM, Abraham MH (1997) J Chem Soc Perkin Trans 2 653

    Google Scholar 

  41. Cativiela C, Garcia JI, Mayoral JA, Salvatella L (1996) Chem Soc Rev 209

    Google Scholar 

  42. Breslow R, Guo T (1988) J Am Chem Soc 110:5613

    Article  CAS  Google Scholar 

  43. Blokzijl W, Engberts JBFN (1992) J Am Chem Soc 114:5440

    Article  CAS  Google Scholar 

  44. Otto S, Blokzijl W, Engberts JBFN (1994) J Org Chem 59:5372

    Article  CAS  Google Scholar 

  45. Blake JF, Jorgersen WL (1991) J Am Chem Soc 113:7430

    Article  CAS  Google Scholar 

  46. Van der Wel GK, Wijnen JW, Engberts JBFN (1996) J Org Chem 61:9001

    Article  Google Scholar 

  47. Wijnen JW, Engberts JBFN (1997) J Org Chem 62:2039

    Article  CAS  Google Scholar 

  48. Lubineau A, Bienaymé H, Queneau Y, Scherrmann MC (1994) New J Chem 18:279

    CAS  Google Scholar 

  49. a) Blake JF, Oakenfull D, Smith MB (1979) Biochemistry 18:5191

    Article  Google Scholar 

  50. b) Lee JC, Timasheff SN (1981) J Biol Chem 256:718

    Google Scholar 

  51. a) Hunt I, Johnson CD (1991) J Chem Soc Perkin Trans 2 1051

    Article  Google Scholar 

  52. b) Braun R, Schuster F, Sauer J (1986) Tetrahedron Lett 27:1285

    Article  CAS  Google Scholar 

  53. Otto S, Engberts JBFN (1995) Tetrahedron Lett 36:2645

    Article  CAS  Google Scholar 

  54. Zhu Z, Espenson JH (1997) J Am Chem Soc 119:3507

    Article  CAS  Google Scholar 

  55. Kobayashi S, Hachiya I, Araki M, Ishitani H (1993) Tetrahedron Lett 34:3755

    Article  CAS  Google Scholar 

  56. Loh T-P, Pei J, Lin M (1996) J Chem Soc Chem Commun 2315

    Google Scholar 

  57. Breslow R, Maitra U, Rideout D (1983) Tetrahedron Lett 24:1901

    Article  CAS  Google Scholar 

  58. Breslow R, Maitra U (1984) Tetrahedron Lett 25:1239

    Article  CAS  Google Scholar 

  59. Diego-Castro MJ, Hailes HC (1998) Tetrahedron Lett 39:2211

    Article  CAS  Google Scholar 

  60. Schneider H-J, Sangwan NK (1987) Angew Chem Int Ed Engl 26:896

    Article  Google Scholar 

  61. Proust SM, Ridley DD (1984) Aust J Chem 37:1677

    Article  CAS  Google Scholar 

  62. Brandes E, Grieco PA, Garner P (1988) J Chem Soc Chem Commun 500

    Google Scholar 

  63. Lubineau A, Augé J, Lubin N (1990) J Chem Soc Perkin Trans 1 3011

    Article  Google Scholar 

  64. Garner PP (1998) Diels-Alder reactions in aqueous media. In: Grieco PA (ed) Organic synthesis in water. Chapman & Hall, London, chap 1

    Google Scholar 

  65. Otto S, Boccaletti G, Engberts JBFN (1998) J Am Chem Soc 120:4238

    Article  CAS  Google Scholar 

  66. Larsen SD, Grieco PA (1985) J Am Chem Soc 107:1768

    Article  CAS  Google Scholar 

  67. Grieco PA, Larsen SD (1986) J Org Chem 51:3553

    Article  CAS  Google Scholar 

  68. Grieco PA, Parker DT (1988) J Org Chem 53:3658

    Article  CAS  Google Scholar 

  69. Waldmann H (1988) Angew Chem Int Ed Engl 27:274

    Article  Google Scholar 

  70. Waldmann H, Braun M (1991) Liebigs Ann Chem 1045

    Google Scholar 

  71. Parker DT (1998) Hetero-Diels-Alders reactions. In:Grieco PA (ed) Organic synthesis in water. Chapman & Hall, London, chap 2

    Google Scholar 

  72. Yu L, Chen D, Wang PG (1996) Tetrahedron Lett 37:2169

    Article  CAS  Google Scholar 

  73. Yu L, Li J, Ramirez J, Chen D, Wang PG (1997) J Org Chem 62:903

    Article  CAS  Google Scholar 

  74. Grieco PA, Bahsas A (1987) J Org Chem 52:5746

    Article  CAS  Google Scholar 

  75. Lubineau A, Augé J, Lubin N (1991) Tetrahedron Lett 32:7529

    Article  CAS  Google Scholar 

  76. Lubineau A, Augé J, Grand E, Lubin N (1994) Tetrahedron Lett 50:10265

    CAS  Google Scholar 

  77. Grieco PA, Henry KJ, Nunes JJ, Matt Jr JE (1992) J Chem Soc Chem Commun 368

    Google Scholar 

  78. Mackeith RA, McCague R, Olivo HF, Palmer CF, Roberts SM (1993) J Chem Soc Perkin Trans 1 313

    Article  Google Scholar 

  79. McCague R, Olivo HF, Roberts SM (1993) Tetrahedron Lett 34:3785

    Article  CAS  Google Scholar 

  80. Burlina F, Favre A, Fourrey J-L, Thomas M (1997) Bio & Med Chem Lett 7:247

    Article  CAS  Google Scholar 

  81. Lubineau A, Augé J, Lubin N (1993) Tetrahedron 49:4639

    Article  CAS  Google Scholar 

  82. Lubineau A, Queneau Y (1995) J Carbohydrate Chem 14:1295

    Article  CAS  Google Scholar 

  83. a) Dignam KJ, Hegarty AF, Quain PL (1978) J Org Chem 43:388

    Article  CAS  Google Scholar 

  84. b) Inoue Y, Araki K, Shiraishi S (1991) Bull Chem Soc Jpn 64:3079

    Article  CAS  Google Scholar 

  85. Wijnen JW, Steiner RA, Engberts JBFN (1995) Tetrahedron Lett 36:5389

    CAS  Google Scholar 

  86. Pandey PS, Pandey IK (1997) Tetrahedron Lett 38:7237

    Article  CAS  Google Scholar 

  87. Lubineau A, Bouchain G, Queneau Y (1995) J Chem Soc Perkin Trans 1 2433

    Article  Google Scholar 

  88. Magnier E, Langlois Y (1998) Tetrahedron Lett 39:837

    Article  CAS  Google Scholar 

  89. Lubineau A, Bouchain G (1997) Tetrahedron Lett 38:8031

    Article  CAS  Google Scholar 

  90. Takaya H, Makino S, Hayakawa Y, Noyori R (1978) J Am Chem Soc 100:1765

    Article  CAS  Google Scholar 

  91. Copley SD, Knowles JR (1987) J Am Chem Soc 109:5008

    Article  CAS  Google Scholar 

  92. White WN, Wolfarth EF (1970) J Org Chem 35:2196

    Article  CAS  Google Scholar 

  93. Coates RM, Rogers BD, Hobbs SJ, Peck DR, Curran DP (1987) J Am Chem Soc 109:1160

    Article  CAS  Google Scholar 

  94. Brandes E, Grieco PA, Gajewski JJ (1989) J Org Chem 54:515

    Article  CAS  Google Scholar 

  95. Gajewski JJ (1997) Acc Chem Res 30:219

    Article  CAS  Google Scholar 

  96. Grieco PA, Brandes EB, McCann S, Clark JD (1989) J Org Chem 54:5849

    Article  CAS  Google Scholar 

  97. Lubineau A, Augé J, Bellanger N, Caillebourdin S (1992) J Chem Soc Perkin Trans 1 1631

    Article  Google Scholar 

  98. Cramer CJ, Truhlar DG (1992) J Am Chem Soc 114:8794

    Article  CAS  Google Scholar 

  99. Severance DL, Jorgensen WL (1992) J Am Chem Soc 114:10966

    Article  CAS  Google Scholar 

  100. Gao J (1994) J Am Chem Soc 116:1563

    Article  CAS  Google Scholar 

  101. Carlson HA, Jorgensen WL (1996) J Am Chem Soc 118:8475

    Article  CAS  Google Scholar 

  102. Barbier P (1898) Comptes Rendus Acad Sci Paris 128:110

    Google Scholar 

  103. Killinger TA, Boughton NA, Runge TA, Wolinsky J (1977) J Organomet Chem 124:131

    Article  CAS  Google Scholar 

  104. Isaac MB and Paquette LA (1997) J Org Chem 62:5333

    Article  CAS  Google Scholar 

  105. Rübsam F, Seck S and Giannis A (1997) Tetrahedron 53:2823

    Article  Google Scholar 

  106. Li CJ (1996) Tetrahedron 52:5643

    Article  CAS  Google Scholar 

  107. Pétrier C, Luche J-L (1985) J Org Chem 50:910

    Article  Google Scholar 

  108. Pétrier C, Einhorn J, Luche J-L (1985) Tetrahedron Lett 26:1449

    Article  Google Scholar 

  109. Durant A, Delplanche JL, Winand R, Reisse J (1995) Tetrahedron Lett 36:4257

    Article  CAS  Google Scholar 

  110. Mattes H, Benezra C (1985) Tetrahedron Lett 26:5697

    Article  CAS  Google Scholar 

  111. Einhorn C, Luche J-L (1987) J Organomet Chem 322:177

    Article  CAS  Google Scholar 

  112. Sjöholm R, Rairama R, Ahonen M (1994) J Chem Soc Chem Commun 1217

    Google Scholar 

  113. Chan TH, Li CJ (1990) Organometallics 9:2649

    Article  CAS  Google Scholar 

  114. Li CJ, Chan TH (1991) Organometallics 10:2548

    Article  CAS  Google Scholar 

  115. Oda Y, Matsuo S, Saiko K (1992) Tetrahedron Lett 33:97

    Article  CAS  Google Scholar 

  116. Bieber LW, Da Silva MF, Da Costa RC, Silva LOS (1998) Tetrahedron Lett 39:3655

    Article  CAS  Google Scholar 

  117. Chan TH, Li CJ (1992) Can J Chem 70:2726

    Article  CAS  Google Scholar 

  118. Waldmann H (1990) Synlett 627

    Google Scholar 

  119. Kunz T, Reissig H-U (1989) Liebiegs Ann Chem 891

    Google Scholar 

  120. Hanessian S, Park H, Yang RY (1997) Synlett 351

    Google Scholar 

  121. Hanessian S, Park H, Yang RY (1997) Synlett 353

    Google Scholar 

  122. Hanessian S, Yang RY (1996) Tetrahedron Lett 37:5273

    Article  CAS  Google Scholar 

  123. Nokami J, Otera J, Sudo T, Okawara R (1983) Organometallics 2:191

    Article  CAS  Google Scholar 

  124. Nokami J, Wakabayashi S, Okawara R (1984) Chem Lett 869

    Google Scholar 

  125. Wu SH, Huang BZ, Zhu TM, Yiao DZ, Chu YL (1990) Act Chim Sinica 48:372

    CAS  Google Scholar 

  126. Schmid W, Whitesides GM (1991) J Am Chem Soc 113:6674

    Article  CAS  Google Scholar 

  127. Kim E, Gordon DM, Schmid W, Whitesides GM (1993) J Org Chem 58:5500

    Article  CAS  Google Scholar 

  128. Uneyama K, Nanbu H, Torii S (1986) Tetrahedron Lett 27:2395

    Article  CAS  Google Scholar 

  129. Masuyama Y, Kishida M, Kurusu Y (1996) Tetrahedron Lett 37:7103

    Article  CAS  Google Scholar 

  130. Houllemare H, Outurquin F, Paulmier C (1997) J Chem Soc Perkin Trans 1 1629

    Article  Google Scholar 

  131. Masuyama Y, Nimura Y, Kurusu Y (1991) Tetrahedron Lett 32:225

    Article  CAS  Google Scholar 

  132. Masuyama Y, Takahara JP, Kurusu Y (1989) Tetrahedron Lett 30:3437

    Article  CAS  Google Scholar 

  133. Wu SH, Huang BZ, Gao X (1990) Synth Commun 20:1279

    Article  CAS  Google Scholar 

  134. Boaretto A, Marton D, Tagliavini G (1985) J Organomet Chem 286:9

    Article  CAS  Google Scholar 

  135. Yanagisawa A, Inoue H, Morodome M, Yamamoto H (1993) J Am Chem Soc 115:10356

    Article  CAS  Google Scholar 

  136. Kobayashi S, Wakabayashi T, Oyamada H (1997) Chem Lett 831

    Google Scholar 

  137. Miyai T, Inoue K, Yasuda M, Baba A (1997) Synlett 699

    Google Scholar 

  138. Belluci C, Cozzi PG, Umani-Ronchi A (1995) Tetrahedron Lett 36:7289

    Article  Google Scholar 

  139. Grieco PA, Bahsas A (1987) J Org Chem 52:1378

    Article  CAS  Google Scholar 

  140. Kobayashi S, Busujima T, Nagayama S (1998) J Chem Soc Chem Commun 19

    Google Scholar 

  141. Li CJ, Chan TH (1991) Tetrahedron Lett 32:7017

    Article  CAS  Google Scholar 

  142. Chan TH, Li CJ, Lee MC, Wei ZY (1994) Can J Chem 72:1181

    Article  CAS  Google Scholar 

  143. Chan TH, Li CJ (1992) J Chem Soc Chem Commun 747

    Google Scholar 

  144. Gordon DM, Whitesides GM (1993) J Org Chem 58:7937

    Article  CAS  Google Scholar 

  145. Choi SK, Lee S, Whitesides GM (1996) J Org Chem 61:8739

    Article  CAS  Google Scholar 

  146. Gao J. Martichonok V, Whitesides GM (1996) J Org Chem 61:9538

    Article  CAS  Google Scholar 

  147. Binder WH, Prenner RH, Schmid W (1994) Tetrahedron 50:749

    Article  CAS  Google Scholar 

  148. Gao J, Härter R, Gordon DM, Whitesides GM (1994) J Org Chem 59:3714

    Article  CAS  Google Scholar 

  149. Araki S, Jin SJ, Idou Y (1992) Bull Chem Soc Jpn 65:1736

    Article  CAS  Google Scholar 

  150. Loh TP, Li XR (1996) J Chem Soc Chem Commun 16:1929

    Google Scholar 

  151. Loh TP, Li XR (1997) Tetrahedron Lett 38:869

    Article  CAS  Google Scholar 

  152. Loh TP, Li XR (1997) Angew Chem Int Ed Engl 36:980

    Article  CAS  Google Scholar 

  153. Isaac MB, Chan TH (1995) Tetrahedron Lett 36:8957

    Article  CAS  Google Scholar 

  154. Diana SCH, Sim KY, Loh TP (1996) Synlett 3:263

    Article  Google Scholar 

  155. Paquette LA, Mitzel TM (1996) J Org Chem 61:8799

    Article  CAS  Google Scholar 

  156. Paquette LA, Mitzel TM (1996) J Am Chem Soc 118:1931

    Article  CAS  Google Scholar 

  157. Paquette LA, Mitzel TM, Isaac MB, Crasto CF, Schomer WW (1997) J Org Chem 62:4293

    Article  CAS  Google Scholar 

  158. Bryan VJ, Chan TH (1996) Tetrahedron Lett 37:5341

    Article  CAS  Google Scholar 

  159. Haberman JX, Li CJ (1997) Tetrahedron Lett 38:4735

    Article  CAS  Google Scholar 

  160. Li CJ, Chen DL, Lu YQ, Haberman JX, Mague JT (1998) Tetrahedron 54:2347

    Article  CAS  Google Scholar 

  161. Bryan VJ, Chan TH (1997) Tetrahedron Lett 38:6493

    Article  CAS  Google Scholar 

  162. Yi XH, Meng Y, Li CJ (1997) Tetrahedron Lett 38:4731

    Article  CAS  Google Scholar 

  163. Jayaraman M, Manhas MS, Bose AK (1997) Tetrahedron Lett 38:709

    Article  CAS  Google Scholar 

  164. Paquette LA, Isaac MB (1998) Heterocycles 47:107

    Article  CAS  Google Scholar 

  165. Yi XH, Meng Y, Li CJ (1998) J Chem Soc Chem Commun 449

    Google Scholar 

  166. Loh TP, Cao GQ, Pei J (1998) Tetrahedron Lett 39:1453

    Article  CAS  Google Scholar 

  167. Capps SM, Lloyd-Jones GC, Murray M, Peakman TM, Walsh KE (1998) Tetrahedron Lett 39:2853

    Article  CAS  Google Scholar 

  168. Loh TP, Ho DSC, Xu KC, Sim KY (1997) Tetrahedron Lett 38:865

    Article  CAS  Google Scholar 

  169. Wada M, Ohki H, Akiba K (1987) J Chem Soc Chem Commun 708

    Google Scholar 

  170. Wada M, Fukuma T, Morioka M, Takahashi T, Miyoshi N (1997) Tetrahedron Lett 38:8045

    Article  CAS  Google Scholar 

  171. Zhou JY, Jia Y, Sun GF, Wu SH (1997) Synth Commun 27:1899

    Article  CAS  Google Scholar 

  172. Ren PD, Jin QH, Yao ZP (1997) Synth Commun 27:2761

    Article  CAS  Google Scholar 

  173. Li CH, Meng Y, Yi XH, Ma J, Chan TH (1997) J Org Chem 62:8632

    Article  CAS  Google Scholar 

  174. Akiyama T, Iwai J (1997) Tetrahedron Lett 38:853

    Article  CAS  Google Scholar 

  175. Pétrier C, Dupuy C, Luche J-L (1986) Tetrahedron Lett 27:3149

    Article  Google Scholar 

  176. Dupuy C, Pétrier C, Sarandeses LA, Luche J-L (1991) Synth Commun 21:643

    Article  CAS  Google Scholar 

  177. Luche J-L, Allavena C (1988) Tetrahedron Lett 29:5373

    Article  CAS  Google Scholar 

  178. Matsumoto K (1981) Angew Chem Int Ed Engl 20:770

    Article  Google Scholar 

  179. Lavallée JF, Deslongchamps P (1988) Tetrahedron Lett 29:6033

    Article  Google Scholar 

  180. Keller E, Feringa BL (1996) Tetrahedron Lett 37:1879

    Article  CAS  Google Scholar 

  181. Keller E, Feringa BL (1997) Synlett 842

    Google Scholar 

  182. Larpent C, Patin H (1988) Tetrahedron 44:6107

    Article  CAS  Google Scholar 

  183. Larpent C, Meignan G, Patin H (1990) Tetrahedron 46:6381

    Article  CAS  Google Scholar 

  184. Lubineau A, Augé J (1992) Tetrahedron Lett 33:8073

    Article  CAS  Google Scholar 

  185. Ballini R, Bosica G (1996) Tetrahedron Lett 37:8027

    Article  CAS  Google Scholar 

  186. Jenner G (1996) Tetrahedron 52:13557

    Article  CAS  Google Scholar 

  187. Augé J, Lubin N, Lubineau A (1994) Tetrahedron Lett 35:7947

    Google Scholar 

  188. Denmark SE, Lee W (1992) Tetrahedron Lett 33:7729

    Article  CAS  Google Scholar 

  189. Nakagawa M, Nakao H, Watanabe KI (1985) Chem. Lett 3:391

    Article  Google Scholar 

  190. Buonora PT, Rosauer KG, Dai L (1995) Tetrahedron Lett 36:4009

    Article  CAS  Google Scholar 

  191. Watanabe KI, Yamada Y, Goto K (1985) Bull Chem Soc Jpn 58:1401

    Article  CAS  Google Scholar 

  192. Zhang Y, Xu W (1989) Synth Commun 19:1291

    Article  CAS  Google Scholar 

  193. Shigemasa Y, Yokohama K, Sashira H, Saimoto H (1994) Tetrahedron Lett 35:1263

    Article  CAS  Google Scholar 

  194. Fringuelli F, Pani G, Piermatti O, Pizzo F (1994) Tetrahedron 50:11499

    Article  CAS  Google Scholar 

  195. Mukaiyama T, Banno K, Narasaka T (1974) J Am Chem Soc 96:7503

    Article  CAS  Google Scholar 

  196. Yamamoto H, Maruyama K, Matsumoto K (1983) J Am Chem Soc 105:6963

    Article  CAS  Google Scholar 

  197. Lubineau A (1986) J Org Chem 51:2142

    Article  CAS  Google Scholar 

  198. Lubineau A, Meyer E (1988) Tetrahedron 44:6065

    Article  CAS  Google Scholar 

  199. Kobayashi S., Hachiya I (1992) Tetrahedron Lett 33:1625

    Article  CAS  Google Scholar 

  200. Kobayashi S, Nagayama S, Busujima T (1997) Chem Lett 959

    Google Scholar 

  201. Loh TP, Pei J, Cao GQ (1996) J Chem Soc Chem Commun 1819

    Google Scholar 

  202. Ishihara K, Hananki N, Yamamoto M (1993) Synlett 577

    Google Scholar 

  203. Kobayashi S, Wakabayashi T, Nagayama S, Oyamada H (1997) Tetrahedron Lett 38:4559

    Article  CAS  Google Scholar 

  204. Tychopoulos V, Tyman JHP (1986) Synth Commun 16:1401

    Article  CAS  Google Scholar 

  205. Larsen SD, Grieco PA, Fobare WF (1986) J Am Chem Soc 108:3512

    Article  CAS  Google Scholar 

  206. Ballini R, Bosica G (1997) J Org Chem 62:425

    Article  CAS  Google Scholar 

  207. Fringuelli F, Germani R, Pizzo F, Savelli G (1989) Tetrahedron Lett 30:1427

    Article  CAS  Google Scholar 

  208. Fringuelli F, Germani R, Pizzo F, Savelli G (1989) Synth Commun 19:1939

    Article  CAS  Google Scholar 

  209. Kirshenbaum KS, Sharpless KB (1985) J Org Chem 50:1979

    Article  CAS  Google Scholar 

  210. Kende AS, Delair P, Blass BE (1994) Tetrahedron Lett 35:8123

    Article  CAS  Google Scholar 

  211. Reed KL, Gupton JT, Solarz TL (1989) Synth Commun 19:3579

    Article  CAS  Google Scholar 

  212. Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB (1987) J Am Chem Soc 109:5765

    Article  CAS  Google Scholar 

  213. Fringuelli F, Germani R, Pizzo F, Santinelli F, Savelli G (1992) J Org Chem 57:1198

    Article  CAS  Google Scholar 

  214. Ye D, Fringuelli F, Piermetti O, Pizzo F (1997) J Org Chem 62:3748

    Article  CAS  Google Scholar 

  215. Kabalka GW, Reddy NK, Narayana C (1992) Tetrahedron Lett 33:865

    Article  CAS  Google Scholar 

  216. Fringuelli F, Germani R, Pizzo F, Savelli G (1989) Gazz Chim Ital 119:249

    CAS  Google Scholar 

  217. Mino T, Masuda S, Nishio M, Yamashita M (1997) J Org Chem 62 2633

    Article  CAS  Google Scholar 

  218. Yang DTC, Zhang CJ, Fu PP, Kabalka GW (1997) Synth Commun 27:1601

    Article  CAS  Google Scholar 

  219. Labinger JA, Herring AM, Bercaw JE (1990) J Am Chem Soc 112:5628

    Article  CAS  Google Scholar 

  220. Ganin E, Amer I (1995) Synth Commun 25:3149

    Article  CAS  Google Scholar 

  221. Okano T, Kaji M, Isotani S, Kiji J (1992) Tetrahedron Lett 33:5547

    Article  CAS  Google Scholar 

  222. Tour JM, Pendalwar SL (1990) Tetrahedron Lett 31:4719

    Article  CAS  Google Scholar 

  223. Tour JM, Cooper JP, Pendalwar SL (1990) J Org Chem 55:3452

    Article  CAS  Google Scholar 

  224. Wan K, Davis ME (1993) Tetrahedron: Asymmetry 4:2461

    Article  CAS  Google Scholar 

  225. Nagel U, Kinzel E (1986) Chem Ber 119:1731

    Article  CAS  Google Scholar 

  226. Sinou D, Safi M, Claver C, Masdeu A (1991) J Mol Catal 68 L9

    Article  CAS  Google Scholar 

  227. Grassert I, Paetzold E, Oehme G (1993) Tetrahedron 49:6605

    Article  CAS  Google Scholar 

  228. Larpent C, Meignan G (1993) Tetrahedron Lett 34:4331

    Article  CAS  Google Scholar 

  229. Benyei A, Joo F (1990) J Mol Catal 58:151

    Article  CAS  Google Scholar 

  230. Grosselin JM, Mercier C (1990) J Mol Catal 63:L25

    Article  CAS  Google Scholar 

  231. Kamochi Y, Kudo T (1994) Chem Pharm Bull 42:402

    CAS  Google Scholar 

  232. Kamochi Y, Kudo T (1995) Chem Pharm Bull 43:1422

    CAS  Google Scholar 

  233. Hasegawa E, Curran DP (1993) J Org Chem 58:5008

    Article  CAS  Google Scholar 

  234. Kamochi Y, Kudo T (1993) Chem Lett 1495

    Google Scholar 

  235. Hannessian S, Girard C (1994) Synlett 861

    Google Scholar 

  236. Maitra U, Sarma KD (1994) Tetrahedron Lett 35:7861

    CAS  Google Scholar 

  237. Light J, Breslow R (1990) Tetrahedron Lett 31:2957

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Chimie Organique Multifonctionnelle, Université de Paris-Sud, bat 420, F-91405, Orsay, France

    André Lubineau

  2. Université de Cergy-Pontoise, 5 mail Gay-Lussac, Neuville-sur-Oise, F-95031, Cergy-Pontoise, France

    Jacques Augé

Authors
  1. André Lubineau
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jacques Augé
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut für Organische Chemie, Ludwig Maximilians-Universität München, Butenanderstr. 5 - 13, D-81377, München, Germany

    Paul Knochel

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Lubineau, A., Augé, J. (1999). Water as Solvent in Organic Synthesis. In: Knochel, P. (eds) Modern Solvents in Organic Synthesis. Topics in Current Chemistry, vol 206. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48664-X_1

Download citation

  • DOI: https://doi.org/10.1007/3-540-48664-X_1

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-66213-6

  • Online ISBN: 978-3-540-48664-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation