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Volumn 62, Issue 2, 1997, Pages 287-291

General Method for Asymmetric Synthesis of α-Methylsulfinyl Ketones: Application to the Synthesis of Optically Pure Oxisuran and Bioisosteres

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EID: 0000678177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961038q     Document Type: Article
Times cited : (36)

References (45)
  • 1
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    • For excellent reviews on the use of chiral sulfoxides in asymmetric synthesis see: (a) Solladié, G. Synthesis 1981, 185. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72. (c) Andersen, K. K. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 3. Drabowicz, J.; Kielbasinski, P.; Mikolaczyk, M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 8. Posner, G. M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 16.
    • (1981) Synthesis , pp. 185
    • Solladié, G.1
  • 2
    • 0001779092 scopus 로고
    • For excellent reviews on the use of chiral sulfoxides in asymmetric synthesis see: (a) Solladié, G. Synthesis 1981, 185. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72. (c) Andersen, K. K. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 3. Drabowicz, J.; Kielbasinski, P.; Mikolaczyk, M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 8. Posner, G. M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 16.
    • (1987) Acc. Chem. Res. , vol.20 , pp. 72
    • Posner, G.H.1
  • 3
    • 1542589162 scopus 로고
    • Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, Chapter 3
    • For excellent reviews on the use of chiral sulfoxides in asymmetric synthesis see: (a) Solladié, G. Synthesis 1981, 185. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72. (c) Andersen, K. K. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 3. Drabowicz, J.; Kielbasinski, P.; Mikolaczyk, M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 8. Posner, G. M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 16.
    • (1988) The Chemistry of Sulfones and Sulfoxides
    • Andersen, K.K.1
  • 4
    • 0004139460 scopus 로고
    • Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, Chapter 8
    • For excellent reviews on the use of chiral sulfoxides in asymmetric synthesis see: (a) Solladié, G. Synthesis 1981, 185. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72. (c) Andersen, K. K. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 3. Drabowicz, J.; Kielbasinski, P.; Mikolaczyk, M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 8. Posner, G. M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 16.
    • (1988) The Chemistry of Sulfones and Sulfoxides
    • Drabowicz, J.1    Kielbasinski, P.2    Mikolaczyk, M.3
  • 5
    • 85033145656 scopus 로고
    • Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, Chapter 16
    • For excellent reviews on the use of chiral sulfoxides in asymmetric synthesis see: (a) Solladié, G. Synthesis 1981, 185. (b) Posner, G. H. Acc. Chem. Res. 1987, 20, 72. (c) Andersen, K. K. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 3. Drabowicz, J.; Kielbasinski, P.; Mikolaczyk, M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 8. Posner, G. M. In The Chemistry of sulfones and sulfoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 16.
    • (1988) The Chemistry of Sulfones and Sulfoxides
    • Posner, G.M.1
  • 6
    • 0001428657 scopus 로고
    • Trost, B. M., Flemming, I., Eds.; Pergamon: Oxford, Chapter 1.5
    • For recent reviews see: (d) Solladié, G. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 1.5. (e) Walker, A. J. Tetrahedron: Asymmetry 1992, 3. (f) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
    • (1991) Comprehensive Organic Synthesis , vol.6
    • Solladié, G.1
  • 7
    • 27144493654 scopus 로고
    • For recent reviews see: (d) Solladié, G. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 1.5. (e) Walker, A. J. Tetrahedron: Asymmetry 1992, 3. (f) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
    • (1992) Tetrahedron: Asymmetry , pp. 3
    • Walker, A.J.1
  • 8
    • 11944251609 scopus 로고
    • For recent reviews see: (d) Solladié, G. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 1.5. (e) Walker, A. J. Tetrahedron: Asymmetry 1992, 3. (f) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
    • (1995) Chem. Rev. , vol.95 , pp. 1717
    • Carreño, M.C.1
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    • A review article on the recently developed methods for the synthesis of optically pure sulfoxides is in preparation
    • A review article on the recently developed methods for the synthesis of optically pure sulfoxides is in preparation
  • 43
    • 0001752993 scopus 로고
    • See for example: Pikul, S.; Raczko, J.; Ankner, K.; Jurczak, J. J. Am. Chem. Soc. 1987, 109, 3981. DeShong, P.; Waltermire, R. E.; Ammon, H. L. J., Am. Chem. Soc. 1988, 110, 1901. Drueckhammer, D. G.; Barbas, C. F., III; Nozaki, K.; Wong, C-H.; Wood, C. Y.; Ciufolini, M. A. J. Org. Chem. 1988, 53, 1607.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3981
    • Pikul, S.1    Raczko, J.2    Ankner, K.3    Jurczak, J.4
  • 44
    • 33845278702 scopus 로고
    • See for example: Pikul, S.; Raczko, J.; Ankner, K.; Jurczak, J. J. Am. Chem. Soc. 1987, 109, 3981. DeShong, P.; Waltermire, R. E.; Ammon, H. L. J., Am. Chem. Soc. 1988, 110, 1901. Drueckhammer, D. G.; Barbas, C. F., III; Nozaki, K.; Wong, C-H.; Wood, C. Y.; Ciufolini, M. A. J. Org. Chem. 1988, 53, 1607.
    • (1988) J., Am. Chem. Soc. , vol.110 , pp. 1901
    • Deshong, P.1    Waltermire, R.E.2    Ammon, H.L.3


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