Skip to main content
SpringerLink
Log in

Monosaccharides as Chiral Auxiliaries and Ligands for Asymmetric Synthesis

  • Reference work entry
Glycoscience

Abstract

This chapter summarizes some recent achievements in asymmetric synthesis, which have been accomplished using sugar derivatives as chiral environments . The use of sugar derivatives as chiral auxiliaries or as chiral ligands of transition-metal catalysts for realizing the asymmetric version of synthetically important organic reactions, such as carbon–carbon bond-forming reactions, the hydrogenation of the carbon–carbon double bond and hydrocyanation, is the focus of this chapter. Prominent studies on these subjects by several research groups are especially emphasized.

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

Access this chapter

Log in via an institution

Institutional subscriptions

Abbreviations

acac:

acetylacetone

BINOL:

1,1′-bi-2‑naphthol

Bn:

benzyl

Boc:

t-butoxycarbonyl

BSA:

N,O-bis(trimethylsilyl)acetamide

iBu:

iso-butyl

tBu:

tert-butyl

COD:

1,5‑cyclooctadiene

de:

diastereomeric excess

DIBAL-H:

diisobutylaluminum hydride

ee:

enantiomeric excess

Et:

ethyl

GABA:

Îł-aminobutyric acid

cHex:

cyclohexyl

HMPA:

hexamethylphosphoramide

LDA:

lithium diisopropylamide

LiHMDS:

lithium hexamethyldisilazide

Me:

methyl

MesCO:

2,4,6‑trimethylbenzoyl

NaHMDS:

sodium hexamethyldisilazide

Napht:

naphthyl

NBS:

N‑bromosuccinimide

NMO:

N‑methylmorpholine-N-oxide

NMR:

nuclear magnetic resonance

Ph:

phenyl

Piv:

tert-butylcarbonyl

cPr:

cyclopropyl

iPr:

iso-propyl

nPr:

n-propyl

RMP:

(R)-2‑methoxymethylpyrrolidine

SMP:

(S)-2‑methoxymethylpyrrolidine

TBS:

tert-butyldimethylsilyl

TFA:

trifluoroacetic acid

THF:

tetrahydrofuran

TIPS:

triisopropylsilyl

TMS:

trimethylsilyl

References

  1. Noyori R (1994) Asymmetric Catalysis in Organic Synthesis. Wiley, New York

    Google Scholar 

  2. Ojima I (ed) (2000) Catalytic Asymmetric Synthesis. Wiley, New York

    Google Scholar 

  3. Jacobsen EN, Pfaltz A, Yamamoto H (eds) (1999) Comprehensive Asymmetric Catalysts. Springer, Berlin Heidelberg New York

    Google Scholar 

  4. Evans DA, Bartroli J, Shin TL (1981) J Am Chem Soc 103:2127

    CAS  Google Scholar 

  5. Evans DA, Ennis MD, Mathre DJ (1982) J Am Chem Soc 104:1737

    CAS  Google Scholar 

  6. Evans DA (1984) In: Morrison JD (ed) Asymmetric Synthesis. Academic Press, New York, 3:1

    Google Scholar 

  7. Lutomski KA, Meyers AI (1984) In: Morrison JD (ed) Asymmetric Synthesis. Academic Press, New York, 3:213

    Google Scholar 

  8. Enders D (1984) In: Morrison JD (ed) Asymmetric Synthesis. Academic Press, New York, 3:275

    Google Scholar 

  9. Evans DA, Britton TC, Ellman JA, Dorow RL (1990) J Am Chem Soc 112:4011

    CAS  Google Scholar 

  10. Oppolzer W (1990) Pure Appl Chem 62:1241

    CAS  Google Scholar 

  11. Groaning MD, Meyers AI (2000) Tetrahedron 56:9643

    Google Scholar 

  12. Cintas P (1991) Tetrahedron 47:6079

    CAS  Google Scholar 

  13. Seyden-Penne J (1995) Chiral Auxiliaries and Ligands in Asymmetric Synthesis. Wiley, New York

    Google Scholar 

  14. Hultin PG, Earle MA, Sudharshan M (1997) Tetrahedron 53:14823

    CAS  Google Scholar 

  15. RĂĽck-Braun K, Kunz H (1999) Chiral Auxiliaries in Cycloaddition. Wiley-VCH, Weinheim

    Google Scholar 

  16. Dwek RA (1996) Chem Rev 96:683

    CAS  Google Scholar 

  17. Vasella A (1977) Helv Chim Acta 60:426

    CAS  Google Scholar 

  18. Vasella A (1977) Helv Chim Acta 60:1273

    CAS  Google Scholar 

  19. Schumacher R, Reissing H-U (1996) Synlett 1121

    Google Scholar 

  20. Tamura O, Mita N, Kusaka N, Suzuki H, Sakamoto M (1997) Tetrahedron Lett 38:429

    CAS  Google Scholar 

  21. Yoshida T, Chika J, Takei H (1998) Tetrahedron Lett 39:4305

    CAS  Google Scholar 

  22. Anaya J, Gero SD, Grande M, Hernando JIM, Laso NM (1999) Bioorg Med Chem 7:837

    CAS  Google Scholar 

  23. Enholm EJ, Gallagher ME, Jiang S, Batson WA (2000) Org Lett 2:3355

    CAS  Google Scholar 

  24. Enholm EJ, Cottone JS, Allais F (2001) Org Lett 3:145

    CAS  Google Scholar 

  25. Vega-PĂ©rez JM, Vega M, Blanco E, Iglesias-Guerra F (2001) Tetrahedron: Asymm 12:3189

    Google Scholar 

  26. Ross GF, Herdtweck E, Ugi I (2002) Tetrahedron 58:6127

    CAS  Google Scholar 

  27. Yu H, Ballard CE, Boyle PD, Wang B (2002) Tetrahedron 58:7663

    CAS  Google Scholar 

  28. Garner P, Anderson JT, Cox PB, Klippenstein SJ, Leslie R, Scardovi N (2002) J Org Chem 67:6195

    CAS  Google Scholar 

  29. Cicchi S, Marradi M, Corsi M, Faggi C, Goti A (2003) Eur J Org Chem 4152

    Google Scholar 

  30. Huang L-L, Xu M-H, Lin G-Q (2005) J Org Chem 70:529

    CAS  Google Scholar 

  31. Kim HJ, Shin E, Chang J, Kim Y, Park YS (2005) Tetrahedron Lett 46:4115

    CAS  Google Scholar 

  32. Zhou G, Zheng W, Wang D, Zhang P, Pan Y (2006) Helv Chim Acta 89:520

    CAS  Google Scholar 

  33. Eguchi T, Kakinuma K (1997) J Syn Org Chem Jpn 55:814

    CAS  Google Scholar 

  34. Kakinuma K, Koudate T, Li H-Y, Eguchi T (1991) Tetrahedron Lett 32:5801

    CAS  Google Scholar 

  35. Eguchi T, Koudate T, Kakinuma K (1993) Tetrahedron 49:4527

    CAS  Google Scholar 

  36. Kakinuma K, Iihama Y, Takagi I, Ozawa K, Yamauchi N, Imamura N, Esumi Y, Uramoto M (1992) Tetrahedron 48:3763

    CAS  Google Scholar 

  37. Kakinuma K, Terasawa H, Li H-Y, Miyazaki K, Oshima T (1993) Biosci Biotech Biochem 57:1916

    CAS  Google Scholar 

  38. Kishida M, Eguchi T, Kakinuma K (1996) Tetrahedron Lett 37:2061

    CAS  Google Scholar 

  39. Maeda Y, Tago K, Eguchi T, Kakinuma K (1996) Biosci Biotech Biochem 60:1248

    CAS  Google Scholar 

  40. Kishida M, Yamauchi N, Sawada K, Ohashi Y, Eguchi T, Kakinuma K (1997) J Chem Soc Perkin Trans 1 891

    Google Scholar 

  41. Yamauchi N, Kishida M, Sawada K, Ohashi Y, Eguchi T, Kakinuma K (1998) Chem Lett 475

    Google Scholar 

  42. Kunz H, Sanger W (1987) Angew Chem Int Ed Engl 26:557

    Google Scholar 

  43. Kunz H, Pfrengle W (1988) J Am Chem Soc 110:651

    CAS  Google Scholar 

  44. Kunz H, Sager W, Pfrengle W, Schanzenbach D (1988) Tetrahedron Lett 29:4397

    CAS  Google Scholar 

  45. Kunz H, Pfrengle W (1988) Tetrahedron 44:5487

    CAS  Google Scholar 

  46. Kunz H, Mohr J (1988) J Chem Soc Chem Commun 1315

    Google Scholar 

  47. Kunz H, Pfrengle W (1989) Angew Chem Int Ed Engl 28:1067

    Google Scholar 

  48. Kunz H, Schanzenbach D (1989) Angew Chem Int Ed Engl 28:1068

    Google Scholar 

  49. Kunz H, Pfrengle W, Sager W (1989) Tetrahedron Lett 30:4109

    CAS  Google Scholar 

  50. Pfrengle W, Kunz H (1989) J Org Chem 54:4261

    CAS  Google Scholar 

  51. Kunz H, RĂĽck K (1993) Angew Chem Int Ed Engl 32:336

    Google Scholar 

  52. Kunz H (1995) Pure Appl Chem 67:1627

    CAS  Google Scholar 

  53. Laschat S, Kunz H (1990) Synlett 51

    Google Scholar 

  54. Laschat S, Kunz H (1990) Synlett 629

    Google Scholar 

  55. Laschat S, Kunz H (1991) J Org Chem 56:5883

    CAS  Google Scholar 

  56. Stähle W, Kunz H (1991) Synlett 260

    Google Scholar 

  57. Kunz H, Sager W, Schanzenbach D, Decker M (1991) Liebigs Ann Chem 649

    Google Scholar 

  58. Kunz H, Pfrengle W, RĂĽck K, Sanger W (1991) Synthesis 1039

    Google Scholar 

  59. Oertel K, Zech G, Kunz H (2000) Angew Chem Int Ed 39:1431

    CAS  Google Scholar 

  60. Laschat S, Kunz H (1992) Synthesis 90

    Google Scholar 

  61. RĂĽck K, Kunz H (1992) Synlett 343

    Google Scholar 

  62. RĂĽck K, Kunz H (1993) Synthesis 1018

    Google Scholar 

  63. Rück-Braun K, Stamm A, Engel S, Kunz H (1997) J Org Chem 62:967

    Google Scholar 

  64. Follmann M, Kunz H (1998) Synlett 989

    Google Scholar 

  65. Weymann M, Schultz-Kulara M, Kunz H (1998) Tetrahedron Lett 39:7835

    CAS  Google Scholar 

  66. Weyman M, Pfrengle W, Schollmeyer D, Kunz H (1997) Synthesis 1151

    Google Scholar 

  67. Weyman M, Schultz-Kukula M, Knauer S, Kunz H (2002) Monatsh Chem 133:57

    Google Scholar 

  68. Kranke B, Hebrault D, Schultz-Kukula M, Kunz H (2004) Synlett 671

    Google Scholar 

  69. Knauer S, Kunz H (2005) Tetrahedron: Asymm 529

    Google Scholar 

  70. Zech G, Kunz H (2003) Angew Chem Int Ed 42:787

    CAS  Google Scholar 

  71. Zech G, Kunz H (2004) Chem Eur J 10:4136

    CAS  Google Scholar 

  72. Klegraf E, Knauer S, Kunz H (2006) Angew Chem Int Ed 45:2623

    CAS  Google Scholar 

  73. Ganz I, Kunz H (1994) Synthesis 1353

    Google Scholar 

  74. Enders D, Heider K-J, Raabe G (1993) Angew Chem Int Ed Engl 32:598

    Google Scholar 

  75. Enders D, Papadopoulos K, Herdtweck E (1993) Tetrahedron 49:1821

    CAS  Google Scholar 

  76. Enders D, Klatt M (1996) Synthesis 1403

    Google Scholar 

  77. Enders D, Berner OM, Vignola N, Bats JW (2001) Chem Commun 2498

    Google Scholar 

  78. Enders D, Berner OM, Vignola N, Harnying W (2002) Synthesis 1945

    Google Scholar 

  79. Enders D, Vignola N, Berner OM, Bats JW (2002) Angew Chem Int Ed 41:109

    CAS  Google Scholar 

  80. Enders D, Vignola N, Berner OM, Harnying W (2005) Tetrahedron 61:3231

    CAS  Google Scholar 

  81. Enders D, Harnying W, Vignola N (2002) Synlett 1727

    Google Scholar 

  82. Enders D, Harnying W, Vignola N (2003) Eur J Org Chem 3939

    Google Scholar 

  83. Enders D, Harnying W, Raabe G (2004) Synthesis 590

    Google Scholar 

  84. Enders D, Harnying W (2004) Synthesis 2910

    Google Scholar 

  85. Enders D, Adelbrecht J-C, Harnying W (2005) Synthesis 2962

    Google Scholar 

  86. Totani, Takao K, Tadano K (2004) Synlett 2066

    Google Scholar 

  87. Totani K, Nagatsuka T, Takao K, Ohba S, Tadano K (1999) Org Lett 1:1447

    CAS  Google Scholar 

  88. Totani K, Nagatsuka T, Yamaguchi S, Takao K, Ohba S, Tadano K (2001) J Org Chem 66:5965

    CAS  Google Scholar 

  89. Totani K, Asano S, Takao K, Tadano K (2001) Synlett 1772

    Google Scholar 

  90. Munakata R, Totani K, Takao K, Tadano K (2000) Synlett 979

    Google Scholar 

  91. Asano S, Tamai T, Totani K, Takao K, Tadano K (2003) Synlett 2252

    Google Scholar 

  92. Sasaki D, Sawamoto D, Takao K, Tadano K, Okue M, Ajito K (2007) Heterocycles 72:103

    CAS  Google Scholar 

  93. Nagatsuka T, Yamaguchi S, Totani K, Takao K, Tadano K (2001) Synlett 481

    Google Scholar 

  94. Nagatsuka T, Yamaguchi S, Totani K, Takao K, Tadano K (2001) J Carbohydr Chem 20:519

    CAS  Google Scholar 

  95. Tamai, T, Asano S, Totani K, Takao K, Tadano K (2003) Synlett 1865

    Google Scholar 

  96. Cullen WR, Sugi Y (1978) Tetrahedron Lett 1635

    Google Scholar 

  97. Jackson R, Thompson DJJ (1978) J Organomet Chem 159:C29

    CAS  Google Scholar 

  98. Seike R (1979) Kinet Catak Lett 10:135

    Google Scholar 

  99. Sinou D, Descotes G (1980) Kinet Catal Lett 14:463

    CAS  Google Scholar 

  100. Inoguchi K, Sakuraba S, Achiwa K (1992) Synlett 169

    Google Scholar 

  101. Morimoto T, Chiba M, Achiwa K (1992) Chem Pharm Bull 40:2894

    CAS  Google Scholar 

  102. Kumar A, Oehme G, Roque JP, Schwarze M, Selke R (1994) Angew Chem Int Ed Engl 33:2197

    Google Scholar 

  103. Buisman GJH, Martin ME, Vos EJ, Klootwijk A, Kamer PCJ, van Leeuwen PWNM (1995) Tetrahedron: Asymm 6:719

    CAS  Google Scholar 

  104. Selke R, Holz J, Riepe A, Börner A (1998) Chem Eur J 4:769

    CAS  Google Scholar 

  105. Gläser B, Kunz H (1998) Synlett 53

    Google Scholar 

  106. Kadyrov R, Heller D, Selke R (1998) Tetrahedron: Asymm 9:329

    CAS  Google Scholar 

  107. Yonehara K, Hashizume T, Ohe K, Uemura S (1998) Bull Chem Soc Jpn 71:1967

    CAS  Google Scholar 

  108. Yonehara K, Hashizume T, Mori K, Ohe K, Uemura S (1999) J Org Chem 64:5593

    CAS  Google Scholar 

  109. Yonehara K, Ohe K, Uemura S (1999) J Org Chem 64:9381

    CAS  Google Scholar 

  110. Suarez A, Pizzano A, Fernandez I, Khiar N (2001) Tetrahedron: Asymm 12:633

    CAS  Google Scholar 

  111. Borriello C, Cucciolito ME, Panunzi A, Ruffo F, Saporito A (2003) Inorg Chem Commun 6:1081

    CAS  Google Scholar 

  112. Reetz MT, Goossen LJ, Meiswinkel A, Paetzold J, Jensen JF (2003) Org Lett 5:3099

    CAS  Google Scholar 

  113. Borriello C, Litto RD, Panunzi A, Ruffo F (2004) Tetrahedron: Asymm 15:681

    CAS  Google Scholar 

  114. Khiar N, Suarez B, Valdivia V, Fernandez I (2005) Synlett 2963

    Google Scholar 

  115. RajanBabu TV, Casalnuovo AL (1992) J Am Chem Soc 114:6265

    CAS  Google Scholar 

  116. RajanBabu TV, Casalnuovo AL (1994) Pure Appl Chem 66:1535

    CAS  Google Scholar 

  117. RajanBabu TV, Ayers TA, Casalnuovo AL (1994) J Am Chem Soc 116:4101

    CAS  Google Scholar 

  118. RajanBabu TV, Ayers TA (1994) Tetrahedron Lett 35:4295

    CAS  Google Scholar 

  119. Casalnuovo AL, RajanBabu TV, Ayers TA, Warren TH (1994) J Am Chem Soc 116:9869

    CAS  Google Scholar 

  120. RajanBabu TV, Casalnuovo AL (1996) J Am Chem Soc 118:6325

    CAS  Google Scholar 

  121. RajanBabu TV, Ayers TA, Halliday GA, You KK, Calabrese JC (1997) J Org Chem 62:6012

    CAS  Google Scholar 

  122. Shin S, RajanBabu TV (1999) Org Lett 1:1229

    CAS  Google Scholar 

  123. RajanBabu TV, Radetich B, You KK, Ayers TA, Casalnuovo AL, Calabrese JC (1999) J Org Chem 64:3429

    CAS  Google Scholar 

  124. Clyne DS, Mermet-Bouvier YC, Nomura N, RajanBabu TV (1999) J Org Chem 64:7601

    CAS  Google Scholar 

  125. Rajanbabu TV, Yan Y-Y, Shin S (2001) J Am Chem Soc 123:10207

    CAS  Google Scholar 

  126. Park H, RajanBabu TV (2002) J Am Chem Soc 124:734

    CAS  Google Scholar 

  127. RajanBabu TV (2003) Chem Rev 103:2845

    CAS  Google Scholar 

  128. Park H, Kumareswaran R, RajanBabu TV (2005) Tetrahedron 61:6352

    CAS  Google Scholar 

  129. Saha B, RajanBabu TV (2006) Org Lett 8:4657

    CAS  Google Scholar 

  130. PĂ mies O, Net G, Ruiz A, Claver C (1999) Tetrahedron: Asymm 10:2007

    Google Scholar 

  131. PĂ mies O, Net G, Ruiz A, Claver C, Woodward S (2000) Tetrahedron: Asymm 11:871

    Google Scholar 

  132. PĂ mies O, Net G, Ruiz A, Claver C (2000) Tetrahedron: Asymm 11:1097

    Google Scholar 

  133. Diéguez M, Pàmies O, Ruiz A, Castillón S, Claver C (2000) Chem Commun 1607

    Google Scholar 

  134. Pàmies O, Diéguez M, Net G, Ruiz A, Claver C (2000) Chem Commun 2383

    Google Scholar 

  135. Pàmies O, Diéguez M, Net G, Ruiz A, Claver C (2000) Tetrahedron: Asymm 11:4377

    Google Scholar 

  136. Diéguez, Jansat S, Gomez M, Ruiz A, Muller G, Claver C (2001) Chem Commun 1132

    Google Scholar 

  137. Pàmies O, Diéguez M, Net G, Ruiz A, Claver C (2001) J Org Chem 66:8364

    Google Scholar 

  138. Diéguez M, Pàmies O, Net G, Ruiz A, Claver C (2001) Tetrahedron: Asymm 12:651

    Google Scholar 

  139. Diéguez M, Ruiz A, Claver C (2001) Tetrahedron: Asymm 12:2895

    Google Scholar 

  140. Diéguez M, Pàmies O, Ruiz A, Castillón S, Claver C (2001) Chem Eur J 7:3086

    Google Scholar 

  141. Diéguez M, Pàmies O, Ruiz A, Claver C (2002) Tetrahedron: Asymm 13:83

    Google Scholar 

  142. Diéguez M, Pàmies O, Ruiz A, Claver C (2002) New J Chem 26:827

    Google Scholar 

  143. Diéguez M, Ruiz A, Claver C (2002) J Org Chem 67:3796

    Google Scholar 

  144. Diéguez M, Ruiz A, Claver C (2003) Dalton Trans 2957

    Google Scholar 

  145. Diéguez M, Pàmies O, Claver C (2004) Chem Rev 104:3189

    Google Scholar 

  146. Guimet E, Diéguez M, Ruiz A, Claver C (2004) Tetrahedron: Asymm 15:2247

    CAS  Google Scholar 

  147. Diéguez M, Pàmies O, Claver C (2005) Chem Commun 1221

    Google Scholar 

  148. Diéguez M, Pàmies O, Claver C (2005) Adv Synth Catal 347:1257

    Google Scholar 

  149. Mata Y, Diéguez M, Pàmies O, Claver C (2005) Adv Synth Catal 347:1943

    CAS  Google Scholar 

  150. Guimet E, Diéguez M, Ruiz A, Claver C (2005) Tetrahedron: Asymm 16:2161

    CAS  Google Scholar 

  151. Diéguez M, Pàmies O, Claver C (2005) Tetrahedron: Asymm 16:3877

    Google Scholar 

  152. Guimet E, Diéguez M, Ruiz A, Claver C (2005) Inorg Chim Acta 358:3824

    CAS  Google Scholar 

  153. Diéguez M, Pàmies O, Claver C (2006) J Organometal Chem 691:2257

    Google Scholar 

  154. Kanai M, Hamashima Y, Shibasaki M (2000) Tetrahedron Lett 41:2405

    CAS  Google Scholar 

  155. Hamashima Y, Kanai M, Shibasaki M (2000) J Am Chem Soc 122:7412

    CAS  Google Scholar 

  156. Manickam G, Nogami H, Kanai M, Gröger H, Shibasaki M (2001) Synlett 617

    Google Scholar 

  157. Hamashima Y, Kanai M, Shibasaki M (2001) Tetrahedron Lett 42:691

    CAS  Google Scholar 

  158. Yabu K, Masumoto S, Yamasaki S, Hamashima Y, Kanai M, Du W, Curran DP, Shibasaki M (2001) J Am Chem Soc 123:9908

    CAS  Google Scholar 

  159. Matsumoto S, Yabu K, Kanai M, Shibasaki M (2002) Tetrahedron Lett 43:2919

    Google Scholar 

  160. Yabu K, Masumoto S, Kanai M, Curran DP, Shibasaki M (2002) Tetrahedron Lett 43:2923

    CAS  Google Scholar 

  161. Masumoto S, Suzuki M, Kanai M, Shibasaki M (2002) Tetrahedron Lett 43:8647

    CAS  Google Scholar 

  162. Fujii K, Maki K, Kanai M, Shibasaki M (2003) Org Lett 5:733

    CAS  Google Scholar 

  163. Takamura M, Yabu K, Nishi T, Yanagisawa H, Kanai M, Shibasaki M (2003) Synlett 353

    Google Scholar 

  164. Yabu K, Matsumoto S, Kanai M, Du W, Curran DP, Shibasaki M (2003) Heterocycles 59:369

    CAS  Google Scholar 

  165. Masumoto S, Usuda H, Suzuki M, Kanai M, Shibasaki M (2003) J Am Chem Soc 125:5634

    CAS  Google Scholar 

  166. Kato N, Suzuki M, Kanai M, Shibasaki M (2004) Tetrahedron Lett 45:3147

    CAS  Google Scholar 

  167. Kato N, Suzuki M, Kanai M, Shibasaki M (2004) Tetrahedron Lett 45:3153

    CAS  Google Scholar 

  168. Masumoto S, Suzuki M, Kanai M, Shibasaki M (2004) Tetrahedron 60:10497

    CAS  Google Scholar 

  169. Kato N, Tomita D, Maki K, Kanai M, Shibasaki M (2004) J Org Chem 69:6128

    CAS  Google Scholar 

  170. Mita T, Sasaki K, Kanai M, Shibasaki M (2005) J Am Chem Soc 127:514

    CAS  Google Scholar 

  171. Kanai M, Kato N, Ichikawa E, Shibasaki M (2005) Synlett 1491

    Google Scholar 

  172. Fukuta Y, Mita T, Fukuda N, Kanai M, Shibasaki M (2006) J Am Chem Soc 128:6312

    CAS  Google Scholar 

  173. Kato N, Mita T, Kanai M, Therrien B, Kawano M, Yamaguchi K, Danjo H, Sei Y, Sato A, Furusho S, Shibasaki M (2006) J Am Chem Soc 128:6768

    CAS  Google Scholar 

  174. Huang H, Chen H, Hu X, Bai C, Zheng Z (2003) Tetrahedron: Asymm 14:297

    CAS  Google Scholar 

  175. Huang H, Zheng Z, Chen H, Bai C, Wang J (2003) Tetrahedron: Asymm 14:1285

    CAS  Google Scholar 

  176. Huang H, Zheng Z, Luo H, Bai C, Hu X, Chen H (2003) Org Lett 5:4137

    CAS  Google Scholar 

  177. Huang H, Zheng Z, Luo H, Bai C, Hu X, Chen H (2004) J Org Chem 69:2355

    CAS  Google Scholar 

  178. Huang H, Liu X, Chen S, Chen H, Zheng Z (2004) Tetrahedron: Asymm 15:2011

    CAS  Google Scholar 

  179. Huang H, Liu X, Chen H, Zheng Z (2005) Tetrahedron: Asymm 16:693

    CAS  Google Scholar 

  180. Emmerson DPG, Villard R, Mugnaini C, Bastsanov A, Howard JAK, Hems WP, Tooze RP, Davis BG (2003) Org Biomol Chem 1:3826

    CAS  Google Scholar 

  181. Emerson DPG, Hems WP, Davis BG (2005) Tetrahedron: Asymm 16:213

    Google Scholar 

  182. Emerson DPG, Hems WP, Davis BG (2006) Org Lett 8:207

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, 351-0198, Saitama, Japan

    Kiichiro Totani

  2. Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, 223-8522, Yokohama, Japan

    Kin-ichi Tadano

Authors
  1. Kiichiro Totani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kin-ichi Tadano
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kin-ichi Tadano .

Editor information

Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

Rights and permissions

Reprints and permissions

Copyright information

© 2008 Springer-Verlag Berlin Heidelberg New York

About this entry

Cite this entry

Totani, K., Tadano, Ki. (2008). Monosaccharides as Chiral Auxiliaries and Ligands for Asymmetric Synthesis . In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_23

Download citation

Publish with us

Policies and ethics

Search

Navigation