Remote stereocontrol by the sulfinyl group: Mukaiyama aldol reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde in the asymmetric synthesis of β-hydroxyacids and 1,3-diols

Tetrahedron

Volumn 62, Issue 52, 2006, Pages 12297-12305

  García Ruano, José L ^a   Fernández Ibáñez, M Ángeles ^a   Maestro, M Carmen ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

1,5 and 1,6 Asymmetric induction; Asymmetric synthesis of 3 hydroxyacids; Chiral sulfoxide; Stereoselective Mukaiyama aldol reaction

Indexed keywords

2 [2 (4 TOLYLSULFINYL)PHENYL]ACETALDEHYDE; ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ESTER DERIVATIVE; HYDROXYACID; SULFUR DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; MUKAIYAMA REACTION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SILYLATION; STEREOCHEMISTRY;

EID: 33750931821     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.010     Document Type: Article

References (66)

1. In: Mahrwald R. (Ed). Modern Aldol Reactions Vols. 1 and 2 (2004), Wiley-VCH, Weinheim
2. Heathcock C.H., Kim B.M., Williams S.F., Masamune S., Rathke M.W., Weipert P., Paterson I., and Gennari C. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 133-319
3. Cowden C.J., and Paterson I. In: Paquette L.A. (Ed). Organic Reactions Vol. 51 (1997), Wiley, New York, NY Chapter 1
4. Mahrwald R. Chem. Rev. 99 (1999) 1095
5. Palomo C., Oiarbide M., and García J.M. Chem.-Eur. J. 8 (2002) 37
6. Palomo C., Oiarbide M., and García J.M. Chem. Soc. Rev. 33 (2004) 65
7. Mukaiyama T., Kobayashi S., and Sano T. Tetrahedron 46 (1990) 4653 and references to previous work
8. Mukaiyama T. Tetrahedron 55 (1999) 8609
9. Review:. Arya P., and Qin H. Tetrahedron 56 (2000) 917
10. Heathcock C.H., and Flippin L.A. J. Am. Chem. Soc. 105 (1983) 1667
11. Annunziata R., Cinquini M., Cozzi F., Cozzi P.G., and Consolandi E. J. Org. Chem. 57 (1992) 456
12. Reviews:. Nelson S.G. Tetrahedron: Asymmetry 9 (1998) 357
13. Machajewski T.D., and Wong C.-H. Angew. Chem., Int. Ed. 39 (2000) 1352
14. Denmark S.E., and Stavenger R.A. Acc. Chem. Res. 33 (2000) 432
15. Carreño M.C. Chem. Rev. 95 (1995) 1717
16. Fernández I., and Khiar N. Chem. Rev. 103 (2003) 3651
17. Pellissier H. Tetrahedron 62 (2006) 5559
18. Mioskowski C., and Solladié G. Tetrahedron 36 (1980) 227
19. Schneider F., and Simon R. Synthesis (1986) 582
20. Annunziata R., Cinquini M., Cozzi F., Montanari F., and Restelli A. Tetrahedron 40 (1984) 3815
21. Butlin R.J., Linney I.D., Critcher D.J., Mahon M.F., Molloy K.C., and Wills M. J. Chem. Soc., Perkin Trans. 1 (1993) 1581
22. García Ruano J.L., Barros D., Maestro M.C., Araya-Maturana R., and Fischer J. J. Org. Chem. 61 (1996) 9462
23. García Ruano J.L., Barros D., Maestro M.C., Alcudia A., and Fernández I. Tetrahedron: Asymmetry 9 (1998) 3445
24. García Ruano J.L., Barros D., Maestro M.C., Slawin A.M.Z., and Page P.C.B. J. Org. Chem. 65 (2000) 6027
25. For alkylation reaction see:
26. Girodier L.D., and Rouessac F.P. Tetrahedron: Asymmetry 5 (1994) 1203
27. Nakamura S., Yasuda H., Watanabe Y., and Toru T. J. Org. Chem. 65 (2000) 8640
28. Nakamura S., Oda M., Yasuda H., and Toru T. Tetrahedron 57 (2001) 8469
29. Almorín A., Carreño M.C., Somoza A., and Urbano A. Tetrahedron Lett. 44 (2003) 5597
30. For hetero Diels-Alder reaction see:. Arai Y., Masuda T., Masaki Y., and Shiro M. Tetrahedron: Asymmetry 7 (1996) 1199
31. For allylation reaction see:
32. Arai Y., Masuda T., Masaki Y., and Koizumi T. Heterocycles 38 (1994) 1751
33. Arai Y., Suzuki A., Masuda T., Masaki Y., and Shiro M. J. Chem. Soc., Perkin Trans. 1 (1995) 2913
34. Arai Y., Masuda T., and Masaki Y. Synlett (1997) 1459
35. Arai Y., Moneda T., Masuda T., and Masaki Y. Heterocycles 53 (2000) 1479
36. García Ruano J.L., Carreño M.C., Toledo M.A., Aguirre J.M., Aranda M.T., and Fischer J. Angew. Chem., Int. Ed. 39 (2000) 2736
37. García Ruano J.L., Alemán J., and Soriano J.F. Org. Lett. 5 (2003) 677
38. García Ruano J.L., and Alemán J. Org. Lett. 5 (2003) 4513
39. García Ruano J.L., Aranda M.T., and Aguirre J.M. Tetrahedron 60 (2004) 5383
40. García Ruano J.L., Alemán J., Aranda M.T., Fernández-Ibáñez M.A., Rodríguez-Fernández M.M., and Maestro M.C. Tetrahedron 60 (2004) 10067
41. García Ruano J.L., Aranda M.T., and Puente M. Tetrahedron 61 (2005) 10099
42. García Ruano J.L., Martín-Castro A.M., Tato F., and Pastor C.J. J. Org. Chem. 70 (2005) 7346
43. García Ruano J.L., Alemán J., and Parra A. J. Am. Chem. Soc. 127 (2005) 13048
44. García Ruano J.L., Martín-Castro A.M., Tato F., and Cárdenas D.J. Tetrahedron: Asymmetry 16 (2005) 1963
45. García Ruano J.L., Fernández-Ibáñez M.A., Maestro M.C., and Rodríguez-Fernández M.M. J. Org. Chem. 70 (2005) 1796
46. García Ruano J.L., Fernández-Ibáñez M.A., Maestro M.C., and Rodriguez-Fernández M.M. Tetrahedron 62 (2006) 1245
47. Evans D.A., Rovis T., Kozlowski M.C., Downey W., and Tedrow J.S. J. Am. Chem. Soc. 122 (2000) 9134
48. It is noteworthy that the use of propanenitrile as the solvent, that would allow to lower the reaction temperature down to -78 °C, and therefore to attain a better diastereoisomeric ratio in relation with that obtained with acetonitrile, was unsuccessful and only trace amounts of the major diastereomer 2a were obtained.
49. Gennari C., and Cozzi P.G. Tetrahedron 44 (1988) 5965
50. Wenzel A.G., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 12964
51. Gennari C., Beretta M.G., Bernardi A., Moro G., Scolastico C., and Todeschini R. Tetrahedron 42 (1986) 893
52. Nakamura E., Shimizu M., Kuwajima I., Sakata J., Yokohama K., and Noyori R. J. Org. Chem. 48 (1983) 932
53. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request, from The Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
54. Gennari C., Bernardi A., Cardani S., and Scolastico C. Tetrahedron Lett. 26 (1985) 797
55. Pettit G.R., and van Tamelen E.E. In: Cope A.C. (Ed). Organic Reactions Vol. 12 (1962), Wiley, New York, NY 356
56. This partial racemization had been reported for other sulfinyl alcohols with Raney Ni. See Ref. 17d.
57. Rech J.C., and Floreancig P.E. Org. Lett. 5 (2003) 1495
58. Dale J.A., and Mosher H.S. J. Am. Chem. Soc. (1973) 512
59. Yamaguchi S. In: Morrison J.D. (Ed). Asymmetric Synthesis Vol. 1 (1983), Academic, New York, NY 125
60. Iseki K., Oishi S., and Kobayashi Y. Tetrahedron 52 (1996) 71
61. Jung J.-C., Kache R., Vines K.K., Zheng Y.-S., Bijoy P., Valluri M., and Avery M.A. J. Org. Chem. 69 (2004) 9269
62. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1991), Wiley, New York, NY p 134
63. Diol (±)-7 has been reported:
64. Gajda T. Synthesis (1987) 1108
65. Ma P., Martin V.S., Masamune S., Sharpless K.B., and Viti S.M. J. Org. Chem. 47 (1982) 1378
66. Tanner D., and Groth T. Tetrahedron 53 (1997) 16139