Skip to main content
SpringerLink
Log in

Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines

  • Chapter
  • First Online:
Bismuth-Mediated Organic Reactions

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 311))

Abstract

Bismuth triflate was found to be an efficient catalyst both in the Mannich-type reaction of silyl enolates and in the Sakurai reaction of allyltrimethylsilane with N-alkoxycarbonylamino sulfones. The reactions proceeded smoothly with a low catalyst loading of Bi(OTf)3·4H2O (0.5–5.0 mol%) to afford the corresponding protected β-amino carbonyl compounds and homoallylic amines in very good yields (up to 96%). The latter compounds could also be obtained via a bismuth-mediated three-component reaction. We have also developed an efficient vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aromatic aldehydes mediated by bismuth triflate in a low catalyst loading (1 mol%). The reaction proceeds rapidly and affords the corresponding 5-[hydroxy(aryl)methyl]furan-2(5H)-ones in high yields with good to very good diastereoselectivities (diastereoisomeric ratios>98:2). Such selectivities, although previously reported with other Lewis acids, could be achieved with a much lower catalyst loading. 5-[Hydroxy(alkyl)methyl]furan-2(5H)-ones derived from ketones could also be obtained with good diastereoselectivities. The vinylogous Mukaiyama aldol reaction has also been extended to 2,2-dimethyl-6-methylene-4-(trimethyl-silyloxy)-1,3-diox-4-ene using 1 mol% of Bi(OTf)3·4H2O.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover 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

References

  1. Puentes CO, Kouznetsov V (2002) J Heterocycl Chem 39:595–614

    Article  CAS  Google Scholar 

  2. Ovaa H, Stragies R, van der Marel GA, van Boom JH, Blechert S (2000) Chem Commun 1501–1502

    Google Scholar 

  3. Lombardo M, Mosconi E, Pasi F, Petrini M, Trombini C (2007) J Org Chem 72:1834–1837

    Article  CAS  Google Scholar 

  4. Giri N, Petrini M, Profeta R (2004) J Org Chem 69:7303–7308

    Article  CAS  Google Scholar 

  5. Zhang J, Wei C, Li C-J (2002) Tetrahedron Lett 43:5731–5733

    Article  CAS  Google Scholar 

  6. Engberts JBFN, Strating J (1965) Recl Trav Chim 84:942–950

    Article  CAS  Google Scholar 

  7. Pizzuti MG, Minnaard AJ, Feringa BL (2008) J Org Chem 73:940–947

    Article  CAS  Google Scholar 

  8. Nakagawa H, Rech JC, Sindelar RW, Ellman JA (2007) Org Lett 9:5155–5157

    Article  CAS  Google Scholar 

  9. Song J, Shih H-W, Deng L (2007) Org Lett 9:603–606

    Article  CAS  Google Scholar 

  10. Lou S, Dai P, Schaus SE (2007) J Org Chem 72:9998–10008

    Article  CAS  Google Scholar 

  11. Marianacci O, Micheletti G, Bernardi L, Fini F, Fochi M, Pettersen D, Sgarzani V, Ricci A (2007) Chem Eur J 13:8338–8351

    Article  CAS  Google Scholar 

  12. Niess B, Jørgensen KA (2007) Chem Commun 1620–1622

    Google Scholar 

  13. Desrosiers J-N, Côté A, Charette AB (2005) Tetrahedron 61:6186–6192

    Article  CAS  Google Scholar 

  14. Palomo C, Oiarbide M, González-Rego MC, Sharma AK, García JM, González A, Landa C, Linden A (2000) Angew Chem Int Ed Engl 39:1063–1065

    Article  CAS  Google Scholar 

  15. Petrini M (2005) Chem Rev 105:3949–3977

    Article  CAS  Google Scholar 

  16. Petrini M, Torregiani E (2005) Tetrahedron Lett 46:5999–6003

    Article  CAS  Google Scholar 

  17. Enders D, Oberbörsch S (2002) Synlett 471–473

    Google Scholar 

  18. Das B, Damodar K, Saritha D, Chowdhury N, Krishnaiah M (2007) Tetrahedron Lett 48:7930–7933

    Article  CAS  Google Scholar 

  19. Kumar RSC, Reddy GV, Babu KS, Rao JM (2009) Chem Lett 38:564–565

    Article  CAS  Google Scholar 

  20. Thirupathi P, Kim SS (2010) Tetrahedron 66:8623–8628

    Article  CAS  Google Scholar 

  21. Schunk S, Enders D (2001) Org Lett 3:3177–3180

    Article  CAS  Google Scholar 

  22. Ogawa C, Azoulay S, Kobayashi S (2005) Heterocycles 66:201–206

    Article  CAS  Google Scholar 

  23. Ollevier T, Lavie-Compin G (2004) Tetrahedron Lett 45:49–52

    Article  CAS  Google Scholar 

  24. Ollevier T, Lavie-Compin G (2002) Tetrahedron Lett 43:7891–7893

    Article  CAS  Google Scholar 

  25. Ollevier T, Nadeau E (2008) Tetrahedron Lett 49:1546–1550

    Article  CAS  Google Scholar 

  26. Kobayashi S, Ogino T, Shimizu H, Ishikawa S, Hamada T, Manabe K (2005) Org Lett 7:4729–4731

    Article  CAS  Google Scholar 

  27. Le Roux C, Ciliberti L, Laurent-Robert H, Laporterie A, Dubac J (1998) Synlett 1249–1251

    Google Scholar 

  28. Ollevier T, Desyroy V, Debailleul B, Vaur S (2005) Eur J Org Chem 4971–4973

    Google Scholar 

  29. Ollevier T, Desyroy V, Nadeau E (2007) ARKIVOC (x):10–20

    Google Scholar 

  30. Ollevier T, Nadeau E, Guay-Bégin A-A (2006) Tetrahedron Lett 47:8351–8354

    Article  CAS  Google Scholar 

  31. Pandey G, Singh RP, Garg A, Singh VK (2005) Tetrahedron Lett 46:2137–2140

    Article  CAS  Google Scholar 

  32. Ollevier T, Li Z (2007) Eur J Org Chem 5665–5668

    Google Scholar 

  33. Komatsu N, Uda M, Suzuki H, Takahashi T, Domae T, Wada M (1997) Tetrahedron Lett 38:7215–7218

    Article  CAS  Google Scholar 

  34. Wieland LC, Zerth HM, Mohan RS (2002) Tetrahedron Lett 43:4597–4600

    Article  CAS  Google Scholar 

  35. Anzalone PW, Baru AR, Danielson EM, Hayes PD, Nguyen MP, Panico AF, Smith RC, Mohan RS (2005) J Org Chem 70:2091–2096

    Article  CAS  Google Scholar 

  36. Leroy B, Markó IE (2002) Org Lett 4:47–50

    Article  CAS  Google Scholar 

  37. Sreekanth P, Park JK, Kim JW, Hyeon T, Kim BM (2004) Catal Lett 96:201–204

    Article  CAS  Google Scholar 

  38. Choudary BM, Chidara S, Raja Sekhar CV (2002) Synlett 1694–1696

    Google Scholar 

  39. Spafford MJ, Christensen JE, Huddle MG, Lacey JR, Mohan RS (2008) Austr J Chem 61:419–421

    Article  CAS  Google Scholar 

  40. Leonard NM, Oswald MC, Freiberg DA, Nattier BA, Smith RC, Mohan RS (2002) J Org Chem 67:5202–5207

    Article  CAS  Google Scholar 

  41. Carrigan MD, Sarapa D, Smith RC, Wieland LC, Mohan RS (2002) J Org Chem 67:1027–1030

    Article  CAS  Google Scholar 

  42. Evans PA, Cui J, Gharpure SJ, Hinkle RJ (2003) J Am Chem Soc 125:11456–11457

    Article  CAS  Google Scholar 

  43. Evans PA, Andrews WJ (2005) Tetrahedron Lett 46:5625–5627

    Article  CAS  Google Scholar 

  44. Qin H, Yamagiwa N, Matsunaga S, Shibasaki M (2007) Chem Asian J 2:150–154

    Article  CAS  Google Scholar 

  45. Qin H, Yamagiwa N, Matsunaga S, Shibasaki M (2006) J Am Chem Soc 128:1611–1614

    Article  CAS  Google Scholar 

  46. Komeyama K, Kouya Y, Ohama T, Takaki K (2011) Chem Commun 47:5031–5033

    Article  CAS  Google Scholar 

  47. Ollevier T, Desyroy V, Asim M, Brochu M-C (2004) Synlett 2794–2796

    Google Scholar 

  48. Ollevier T, Mwene-Mbeja TM (2008) Can J Chem 86:209–212

    Article  CAS  Google Scholar 

  49. Ollevier T, Mwene-Mbeja TM (2006) Synthesis 3963–3966

    Google Scholar 

  50. Suzuki H, Matano Y (2001) Organobismuth chemistry. Elsevier, Amsterdam

    Google Scholar 

  51. Gaspard-Iloughmane H, Le Roux C (2004) Eur J Org Chem 2517–2532

    Google Scholar 

  52. Leonard NM, Wieland LC, Mohan RS (2002) Tetrahedron 58:8373–8397

    Article  CAS  Google Scholar 

  53. Hua R (2008) Curr Org Synth 5:1–27

    Article  CAS  Google Scholar 

  54. Ollevier T, Nadeau E, Desyroy V (2009) Bismuth(III) trifluoromethanesulfonate. In: Fuchs PL (ed) Electronic encyclopedia of reagents for organic synthesis (e-EROS). Wiley, Chichester. http://onlinelibrary.wiley.com/o/eros/articles/rn00959/frame.html.Accessed22Sep2011

  55. Salvador JAR, Pinto RMA, Silvestre SM (2009) Mini-Reviews in Organic Chemistry 6:241–274

    Article  CAS  Google Scholar 

  56. Mohan R (2010) Nat Chem 2:336

    Article  CAS  Google Scholar 

  57. Ollevier T, Li Z (2006) Org Biomol Chem 4:4440–4443

    Article  CAS  Google Scholar 

  58. Ollevier T, Nadeau E, Eguillon J-C (2006) Adv Synth Catal 348:2080–2084

    Article  CAS  Google Scholar 

  59. Brocherieux-Lanoy S, Dhimane H, Poupon J-C, Vanucci C, Lhommet G (1997) J Chem Soc Perkin Trans 1 2163–2164

    Google Scholar 

  60. Maier ME, Lapeva T (1998) Synlett 891–893

    Google Scholar 

  61. Dangles O, Guibé F, Balavoine G, Lavielle S, Marquet A (1987) J Org Chem 52:4984–4993

    Article  CAS  Google Scholar 

  62. Dewi-Wülfing P, Gebauer J, Blechert S (2006) Synlett 487–489

    Google Scholar 

  63. Braekman J-C, Charlier A, Daloze D, Heilporn S, Pasteels J, Plasman V, Wang S-F (1999) Eur J Org Chem 1749–1755

    Google Scholar 

  64. Kubizna P, Špánik I, Kožíšek J, Szolcsányiš P (2010) Tetrahedron 66:2351–2355

    Article  CAS  Google Scholar 

  65. Kobayashi S, Araki M, Ishitani H, Nagayama S, Hachiya I (1995) Synlett 233–234

    Google Scholar 

  66. Kobayashi S, Araki M, Yasuda M (1995) Tetrahedron Lett 36:5773–5776

    CAS  Google Scholar 

  67. Kobayashi S, Busujima T, Nagayama S (1999) Synlett 545–546

    Google Scholar 

  68. Kobayashi S, Moriwaki M, Akiyama R, Suzuki S, Hachiya I (1996) Tetrahedron Lett 37:7783–7786

    Article  CAS  Google Scholar 

  69. Kobayashi S, Ueno M (2004) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis. Springer, Berlin, Supplement 1

    Google Scholar 

  70. Córdova A (2004) Acc Chem Res 37:102–112

    Article  CAS  Google Scholar 

  71. Arend M, Westermann B, Risch N (1998) Angew Chem Int Ed Engl 37:1044–1070

    Article  Google Scholar 

  72. Kobayashi S, Sugiura M, Kitagawa H, Lam WW-L (2002) Chem Rev 102:2227–2302

    Article  CAS  Google Scholar 

  73. Kobayashi S, Ishitani H (1999) Chem Rev 99:1069–1094

    Article  CAS  Google Scholar 

  74. Kobayashi S, Hirano K, Sugiura M (2005) Chem Commun 104–106

    Google Scholar 

  75. Shibata I, Nose K, Sakamoto K, Yasuda M, Baba A (2004) J Org Chem 69:2185–2187

    Article  CAS  Google Scholar 

  76. Ding H, Friestad GK (2004) Synthesis 2216–2221

    Google Scholar 

  77. Kobayashi S, Sugiura M, Ogawa C (2004) Adv Synth Catal 346:1023–1034

    Article  CAS  Google Scholar 

  78. Li S-W, Batey RA (2004) Chem Commun 1382–1383

    Google Scholar 

  79. Yamasaki S, Fujii K, Wada R, Kanai M, Shibasaki M (2002) J Am Chem Soc 124:6536–6537

    Article  CAS  Google Scholar 

  80. Andrade CKZ, Azevedo NR, Oliveira GR (2002) Synthesis 928–936

    Google Scholar 

  81. Hirabayashi R, Ogawa C, Sugiura M, Kobayashi S (2001) J Am Chem Soc 123:9493–9499

    Article  CAS  Google Scholar 

  82. Friestad GK, Ding H (2001) Angew Chem Int Ed Engl 40:4491–4493

    Article  CAS  Google Scholar 

  83. Akiyama T, Sugano M, Kagoshima H (2001) Tetrahedron Lett 42:3889–3892

    Article  CAS  Google Scholar 

  84. Gastner T, Ishitani H, Akiyama R, Kobayashi S (2001) Angew Chem Int Ed Engl 40:1896–1898

    Article  CAS  Google Scholar 

  85. Schaus JV, Jain N, Panek JS (2000) Tetrahedron 56:10263–10274

    Article  CAS  Google Scholar 

  86. Akiyama T, Iwai J, Onuma Y, Kagoshima H (1999) Chem Commun 2191–2192

    Google Scholar 

  87. Kobayashi S, Sugita K, Oyamada H (1999) Synlett 138–140

    Google Scholar 

  88. Nakamura H, Nakamura K, Yamamoto Y (1998) J Am Chem Soc 120:4242–4243

    Article  CAS  Google Scholar 

  89. Jain NF, Takenaka N, Panek JS (1996) J Am Chem Soc 118:12475–12476

    Article  CAS  Google Scholar 

  90. Smitha G Miriyala B, Williamson JS (2005) Synlett 839–841

    Google Scholar 

  91. Phukan P (2004) J Org Chem 69:4005–4006

    Article  CAS  Google Scholar 

  92. Ella-Menye J-R, Dobbs W, Billet M, Klotz P, Mann A (2005) Tetrahedron Lett 46:1897–1900

    Article  CAS  Google Scholar 

  93. Sugiura M, Hirano K, Kobayashi S (2004) J Am Chem Soc 126:7182–7183

    Article  CAS  Google Scholar 

  94. Choudary BM, Jyothi K, Madhi S, Kantam ML (2004) Synlett 231–234

    Google Scholar 

  95. Akiyama T, Onuma Y (2002) J Chem Soc Perkin Trans 1 1157–1158

    Google Scholar 

  96. Yadav JS, Reddy BVS, Raju AK, Gnaneshwar D (2002) Adv Synth Catal 344:938–940

    Article  CAS  Google Scholar 

  97. Aspinall HC, Bissett JS, Greeves N, Levin D (2002) Tetrahedron Lett 43:323–325

    Article  CAS  Google Scholar 

  98. Yadav JS, Reddy BVS, Reddy PSR, Shesha Rao M (2002) Tetrahedron Lett 43:6245–6247

    Article  CAS  Google Scholar 

  99. Liu J, Wong C-H (2002) Tetrahedron Lett 43:3915–3917

    Article  CAS  Google Scholar 

  100. Billet M, Klotz P, Mann A (2001) Tetrahedron Lett 42:631–634

    Article  CAS  Google Scholar 

  101. Niimi L, Serita K-I, Hiraoka S, Yokozawa T (2000) Tetrahedron Lett 41:7075–7078

    Article  CAS  Google Scholar 

  102. Masuyama Y, Tosa J, Kurusu Y (1999) Chem Commun 1075–1076

    Google Scholar 

  103. Kobayashi S, Busujima T, Nagayama S (1998) Chem Commun 19–20

    Google Scholar 

  104. Akiyama T, Iwai J (1998) Synlett 273–274

    Google Scholar 

  105. Veenstra SJ, Schmid P (1997) Tetrahedron Lett 38:997–1000

    Article  CAS  Google Scholar 

  106. Zheng Y-F, Lu G-L, Zhang Y-M (2000) Youji Huaxue 20:551–552

    CAS  Google Scholar 

  107. Choudary BM, Chidara S, Sekhar CVR (2002) Synlett 1694–1696

    Google Scholar 

  108. Ollevier T, Ba T (2003) Tetrahedron Lett 44:9003–9005

    Article  CAS  Google Scholar 

  109. Ollevier T, Nadeau E (2007) Org Biomol Chem 5:3126–3134

    Article  CAS  Google Scholar 

  110. Ollevier T, Nadeau E (2004) J Org Chem 69:9292–9295

    Article  CAS  Google Scholar 

  111. Ollevier T, Nadeau E (2006) Synlett 219–222

    Google Scholar 

  112. Kagan HB, Basselier J-J, Luche J-L (1964) Tetrahedron Lett 5:941–948

    Article  Google Scholar 

  113. Gennari C, Venturini I, Gislon G, Schimperna G (1987) Tetrahedron Lett 28:227–230

    Article  CAS  Google Scholar 

  114. Amii H, Kishikawa Y, Kageyama K, Uneyama (2000) J Org Chem 65:3404–3408

    Article  CAS  Google Scholar 

  115. Shiina I (2004) In: Mahrwald R (ed) Modern aldol reactions. Wiley-VCH, Weinheim

    Google Scholar 

  116. Mukaiyama T, Narasaka K, Banno K (1973) Chem Lett 1011–1014

    Google Scholar 

  117. Mukaiyama T, Banno K, Narasaka K (1974) J Am Chem Soc 96:7503–7509

    Article  CAS  Google Scholar 

  118. Mukaiyama T, Matsuo J-i (2004) In: Mahrwald R (ed) Modern aldol reactions. Wiley-VCH, Weinheim

    Google Scholar 

  119. Carreira EM (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis I–III. Springer, Berlin

    Google Scholar 

  120. Casiraghi G, Zanardi F, Appendino G, Rassu G (2000) Chem Rev 100:1929–1972

    Article  CAS  Google Scholar 

  121. Denmark SE, Heemstra JR Jr, Beutner GL (2005) Angew Chem Int Ed Engl 44:4682–4698

    Article  CAS  Google Scholar 

  122. Matsuoka Y, Irie R, Katsuki T (2003) Chem Lett 32:584–585

    Article  CAS  Google Scholar 

  123. Szlozek M, Figadère B (2000) Angew Chem Int Ed Engl 39:1799–1801

    Article  Google Scholar 

  124. Szlozek M, Franck X, Figadère B, Cavé A (1998) J Org Chem 63:5169–5172

    Article  Google Scholar 

  125. Palombi L, Acocella MR, Celenta N, Massa A, Villano R, Scettri A (2006) Tetrahedron: Asymmetry 17:3300–3303

    Article  CAS  Google Scholar 

  126. Nagao H, Yamane Y, Mukaiyama T (2007) Chem Lett 36:8–9

    Article  CAS  Google Scholar 

  127. Kobayashi S, Hamada T, Nagayama S, Manabe K (2001) Org Lett 3:165–167

    Article  CAS  Google Scholar 

  128. Kobayashi S, Hachiya I, Takahori T (1993) Synthesis 371–373

    Google Scholar 

  129. Kobayashi S, Hachiya I (1992) Tetrahedron Lett 33:1625–1628

    Article  CAS  Google Scholar 

  130. Casiraghi G, Zanardi F, Battistini L, Rassu G (2009) Synlett 1525–1542

    Google Scholar 

  131. Casiraghi G, Rassu G (1995) Synthesis 607–626

    Google Scholar 

  132. Jefford CW, Jaggi D, Boukouvalas J (1987) Tetrahedron Lett 28:4037–4040

    Article  CAS  Google Scholar 

  133. Acocella MR, De Rosa M, Massa A, Palombi L, Villano R, Scettri A (2005) Tetrahedron 61:4091–4097

    Article  CAS  Google Scholar 

  134. Kong K, Romo D (2006) Org Lett 8:2909–2912

    Article  CAS  Google Scholar 

  135. Yoshii E, Koizumi T, Kitatsuji E, Kawazoe T, Kaneko T (1976) Heterocycles 4:1663–1668

    Article  CAS  Google Scholar 

  136. Boukouvalas J, Maltais F, Lachance N (1994) Tetrahedron Lett 35:7897–7900

    CAS  Google Scholar 

  137. López CS, Álvarez R, Vaz B, Faza ON, de Lera AR (2005) J Org Chem 70:3654–3659

    Article  CAS  Google Scholar 

  138. Sarma KD, Zhang J, Curran TT (2007) J Org Chem 72:3311–3318

    Article  CAS  Google Scholar 

  139. Yadav JS, Subba Reddy BV, Narasimhulu G, Satheesh G (2008) Tetrahedron Lett 49:5683–5686

    Article  CAS  Google Scholar 

  140. Raders SM, Verkade JG (2009) J Org Chem 74:5417–5428

    Article  CAS  Google Scholar 

  141. De Rosa M, Citro L, Soriente A (2006) Tetrahedron Lett 47:8507–8510

    Article  CAS  Google Scholar 

  142. von der Ohe F, Brückner R (2000) New J Chem 24:659–669

    Article  Google Scholar 

  143. von der Ohe F, Brückner R (1998) Tetrahedron Lett 39:1909–1910

    Article  Google Scholar 

  144. Görth FC, Umland A, Brückner R (1998) Eur J Org Chem 1055–1062

    Google Scholar 

  145. Görth FC, Brückner R (1999) Synthesis 1520–1528

    Google Scholar 

  146. Ollevier T, Bouchard J-E, Desyroy V (2008) J Org Chem 73:331–334

    Article  CAS  Google Scholar 

  147. Naito S, Escobar M, Kym PR, Liras S, Martin SF (2002) J Org Chem 67:4200–4208

    Article  CAS  Google Scholar 

  148. Pelter A, Al-Bayati R, Lewis W (1982) Tetrahedron Lett 23:353–356

    Article  CAS  Google Scholar 

  149. Asaoka M, Yanagida N, Ishibashi K, Takei H (1981) Tetrahedron Lett 22:4269–4270

    Article  CAS  Google Scholar 

  150. Singer RA, Carreira EM (1995) J Am Chem Soc 117:12360–12361

    Article  CAS  Google Scholar 

  151. Krüger J, Carreira EM (1998) J Am Chem Soc 120:837–838

    Article  Google Scholar 

  152. Denmark SE, Beutner GL (2003) J Am Chem Soc 125:7800–7801

    Article  CAS  Google Scholar 

  153. Denmark SE, Beutner GL (2005) J Am Chem Soc 127:3774–3789

    Article  CAS  Google Scholar 

  154. De Rosa M, Soriente A, Scettri A (2000) Tetrahedron: Asymmetry 11:3187–3195

    Article  Google Scholar 

  155. Sato M, Sugita Y, Abiko Y, Kaneko C (1992) Tetrahedron: Asymmetry 3:1157–1160

    Article  CAS  Google Scholar 

  156. Sugita Y, Sakaki J-i, Sato M, Kaneko C (1992) J Chem Soc Perkin Trans 1 2855–2861

    Google Scholar 

  157. Bach T, Kirsch S (2001) Synlett 2001:1974–1976

    Google Scholar 

  158. Acocella MR, De Rosa M, Massa A, Palombi L, Villano R, Scretti A (2005) Tetrahedron 61:4091–4097

    Article  CAS  Google Scholar 

  159. Ollevier T, Desyroy V, Catrinescu C, Wischert R (2006) Tetrahedron Lett 47:9089–9092

    Article  CAS  Google Scholar 

Download references

Acknowledgments

I deeply thank my co-workers, whose names are listed in the references, for their significant contribution to the chemistry described herein. Most of the research projects were supported by the Natural Sciences and Engineering Research Council of Canada (NSERC).

Author information

Authors and Affiliations

  1. Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada, G1V 0A6

    Thierry Ollevier

Authors
  1. Thierry Ollevier
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Thierry Ollevier .

Editor information

Editors and Affiliations

  1. Dépt. Chimie, Université Laval, avenue de la Médecine 1045, Quebec, G1V 0A6, Québec, Canada

    Thierry Ollevier

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Ollevier, T. (2011). Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines. In: Ollevier, T. (eds) Bismuth-Mediated Organic Reactions. Topics in Current Chemistry, vol 311. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_298

Download citation

Publish with us

Policies and ethics

Search

Navigation