Skip to main content
SpringerLink
Log in
Book cover

Aldol Reactions pp 83–95Cite as

Tin Lewis Acids

  • Chapter

  • 1596 Accesses

In their initial experiments Mukaiyama and coworkers found even tin(IV) chloride to be a promising Lewis acid. Tin(IV) chloride proved to be a mild active Lewis acid with good chelation properties.1,2,3,4,5 Systematic studies concerning stereo-selectivities were conducted by Heathcock6,7,8 and Reetz.9,10,11,12 For comprehensive, up-to-date overview see Shiina and Fukui.13 In contrast to the methods described above the stereoselectivities were strongly influenced by oxygen functionalities of the aldehydes used. These results are summarized in Scheme 3.1.2.1.

This is a preview of subscription content, 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   129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   169.99
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

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Mukaiyama T, Narasaka K, Banno K (1973) Chem Lett 1011

    Google Scholar 

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

    Article  CAS  Google Scholar 

  3. Saigo K, Osaki M, Mukaiyama T (1975) Chem Lett 989

    Google Scholar 

  4. Mukaiyama T (1982) Org React 28:203

    CAS  Google Scholar 

  5. Mukaiyama T, Narasaka K (1987) Org Synth 65:6

    CAS  Google Scholar 

  6. Heathcock CH, Hug KT, Flippin LA (1984) Tetrahedron Lett 25:5973

    Article  CAS  Google Scholar 

  7. Heathcock CH, Davidsen K, Hug KT, Filippin LA (1986) J Org Chem 51:3027

    Article  CAS  Google Scholar 

  8. Heathcock CH, Montgomery SH (1985) Tetrahedron Lett 26:1001

    Article  CAS  Google Scholar 

  9. Reetz MT, Kesseler K, Jung A (1984) Tetrahedron Lett 25:729

    Article  CAS  Google Scholar 

  10. Reetz MT, Kesseler K, Jung A (1984) Tetrahedron 40:4327

    Article  CAS  Google Scholar 

  11. Reetz MT, Kesseler K, Schmidtberger BW, Steinbach R (1983) Angew Chem Int Ed Engl 22:989

    Article  Google Scholar 

  12. Reetz MT, Kesseler K (1985) J Org Chem 50:5434

    Article  CAS  Google Scholar 

  13. Shiina I, Fukui H (2008) In: Acid Catalysis in Modern Organic Synthesis, Yamamoto H, Ishihara K (eds). Wiley, Weinheim, vol 1, p 537

    Google Scholar 

  14. Gennari C, Bernardi A, Poli G, Scolastico C (1985) Tetrahedron Lett 26:2373

    Article  CAS  Google Scholar 

  15. Gennari C, Beretta MG, Bernardi A, Moro G, Scolastico C, Todeschini R (1986) Tetrahedron 42:893

    Article  CAS  Google Scholar 

  16. Gennari C, Cozzi PG (1988) Tetrahedron 44:5965

    Article  CAS  Google Scholar 

  17. Ewing WR, Harris BD, Li WR, Joullié MM (1989) Tetrahedron Lett 30:3757

    Article  CAS  Google Scholar 

  18. Li WR, Ewing WR, Harris BD, Joullié MM (1990) J Am Chem Soc 112:7659

    Article  CAS  Google Scholar 

  19. Danishefsky SJ, DeNinno SL, Chen S. Boisvert L, Barbachyn M (1989) J Am Chem Soc 111:5810

    Article  CAS  Google Scholar 

  20. Danishefsky S, Barbachyn M (1985) J Am Chem Soc 107:7761

    Article  CAS  Google Scholar 

  21. Mukai C, Moharram SM, Kataoka O, Hanaoka M (1995) J Chem Soc Perkin Trans 1:2849

    Article  Google Scholar 

  22. Mukaiyama T, Iwasawa N, Stevens RW, Haga T (1984) Tetrahedron 40:1381

    Article  CAS  Google Scholar 

  23. Iwasawa N, Mukaiyama T (1982) Chem Lett 1441

    Google Scholar 

  24. Kobayashi S, Mukaiyama T (1989) Chem Lett 297

    Google Scholar 

  25. Kobayashi S, Uchiro H, Fujishita Y, Shiina I, Mukaiyama T (1991) J Am Chem Soc 113:4247

    Article  CAS  Google Scholar 

  26. Mukaiyama T, Kobayashi S (1990) J Organomet Chem 382:39

    Article  CAS  Google Scholar 

  27. Mukaiyama T, Uchiro H, Shiina I, Kobayashi S (1990) Chem Lett 1019

    Google Scholar 

  28. Mukaiyama T, Shiina I, Kobayashi S (1991) Chem Lett 1902

    Google Scholar 

  29. Mukaiyama T, Anan H, Shiina I, Kobayahi S (1993) Bull Soc Chim Fr 130:388

    CAS  Google Scholar 

  30. Mukaiyama T, Shiina I, Uchiro H, Kobayashi S (1994) Bull Chem Soc Jpn 67:1708

    Article  CAS  Google Scholar 

  31. Mukaiyama T, Shiina I, Kobayashi S (1990) Chem Lett 2201

    Google Scholar 

  32. Kobayashi S, Kawasuji T (1993) Synlett 911

    Google Scholar 

  33. Kanda Y, Fukuyama T (1993) J Am Chem Soc 115:8451

    Article  CAS  Google Scholar 

  34. White JD, Deerberg J (1997) Chem Commun 1919

    Google Scholar 

  35. Kobayashi S, Furuta T (1998) Tetrahedron 54:10275

    Article  CAS  Google Scholar 

  36. Kobayashi S, Hayashi T, Kawasuji T (1994) Tetrahedron Lett 35:9573

    Article  CAS  Google Scholar 

  37. Mukaiyama T, Shiina I, Iwadare H, Saitoh M, Nishimura T, Ohkawa N, Sakoh H, Nishimura K, Tani Y, Hasegawa M, Yamada K, Saitoh K (1999) Chem Eur J 5:121

    Article  CAS  Google Scholar 

  38. Shiina I, Fujisawa H, Ishii T, Fukuda Y (2000) Heterocycles 52:1105

    Article  CAS  Google Scholar 

  39. Shiina I, Fukuda Y, Ishii T, Fujisawa H, Mukaiyama T (1998) Chem Lett 831

    Google Scholar 

  40. Shiina I, Oshiumi H, Hashizume M, Yamai Y, Ibuka R (2004) Tetrahedron Lett 45:543

    Article  CAS  Google Scholar 

  41. Shiina I, Kubota M, Oshiumi H, Hashizume M, (2004) J Org Chem 69:822

    Article  Google Scholar 

  42. Shiina I, Hashizume M, Yamai YS, Oshiumi H, Shimazaki T, Takasuna YJ, Ibuka R (2005) Chem Eur J 11:6601

    Article  CAS  Google Scholar 

  43. Shiina I (2004) In Modern Aldol Reactions, Mahrwald R (ed). Wiley-VCH, Weinheim, vol 2, p 105

    Chapter  Google Scholar 

  44. Mukaiyama T, Kobayashi S, Uchiro H, Shiina I (1990) Chem Lett 129

    Google Scholar 

  45. Kobayashi S, Fujishita Y, Mukaiyama T (1990) Chem Lett 1455

    Google Scholar 

  46. Kobayashi S, Horibe M, Saito Y (1994) Tetrahedron 50:9629

    Article  CAS  Google Scholar 

  47. Kobayashi S, Fujishita Y, Mukaiyama T (1989) Chem Lett 2069

    Google Scholar 

  48. Evans DA, MacMillan DWC, Campos KR (1997) J Am Chem Soc 119:10859

    Article  CAS  Google Scholar 

  49. Evans DA, Wu J, Masse CE, MacMillan DWC (2002) Org Lett 4:3379

    Article  CAS  Google Scholar 

  50. Johnson JS, Evans DA (2000) Acc Chem Res 33:325

    Article  CAS  Google Scholar 

  51. Kobayashi S, Furuta T, Hayashi T, Nishijima M, Hanada K (1998) J Am Chem Soc 120:908

    Article  CAS  Google Scholar 

  52. Evans DA, Cee VJ, Smith TE, Fitch DM, Cho PS (2000) Angew Chem Int Ed Engl 39:2533

    Article  CAS  Google Scholar 

  53. Evans DA, Fitch DM (2000) Angew Chem Int Ed Engl 39:2536

    Article  CAS  Google Scholar 

  54. Evans DA, Wu J, Masse CE, MacMillan DWC (2002) Org Lett 4:3379

    Article  CAS  Google Scholar 

  55. Jung ME, Zhang, TH (2008) Org Lett 10:137

    Article  CAS  Google Scholar 

  56. Angell P, Zhang J, Belmont D, Curran T, Davidson JG (2005) Tetrahedron Lett 46:2029

    Article  CAS  Google Scholar 

  57. Nakamura S, Sato H, Hirata Y, Watanabe N, Hashimoto S (2005) Tetrahedron 61:11078

    Article  CAS  Google Scholar 

  58. White DJ, Deerberg J (1997) Chem Commun 1919

    Google Scholar 

  59. Nicolaou KC (1996) In: Classics in Total Synthesis, Nicolaou KC, Sorensen EJ (eds). Wiley-VCH, Weinheim, p 565

    Google Scholar 

  60. Shiina I, Oshiumi H, Hashizume M, Yamai Y, Ibuka R (2004) Tetrahedron Lett 45:543

    Article  CAS  Google Scholar 

  61. Shiina I, Kubota M, Oshiumi H, Hashizume M (2004) J Org Chem 69:1822

    Article  CAS  Google Scholar 

  62. Shiina I, Hashizume M, Yamai YS, Oshiumi H, Shimazaki T, Takasuna YJ, Ibuka R (2005) Chem Eur J 11:6601

    Article  CAS  Google Scholar 

  63. Shiina I (2007) Chem Rev 107:239

    Article  CAS  Google Scholar 

  64. Evans DA, Trotter BW, Coleman PJ, Cote B, Dias LC, Rajapakse HA, Tyler AN (1999) Tetrahedron 55:8671

    Article  CAS  Google Scholar 

  65. Evans DA, Fitch, DM, Smith TE, Cee, VJ (2000) J Am Chem Soc 122:10033

    Article  CAS  Google Scholar 

Download references

Editor information

Editors and Affiliations

  1. Institute of Chemistry, Humboldt University, Brook Taylor Str. 2, Berlin, 12 489, Germany

    Rainer Mahrwald

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer Science+Business Media B.V

About this chapter

Cite this chapter

(2009). Tin Lewis Acids. In: Mahrwald, R. (eds) Aldol Reactions. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8701-1_9

Download citation

Publish with us

Policies and ethics

Search

Navigation