메뉴 건너뛰기




Volumn 53, Issue 37, 1997, Pages 12469-12486

The organoselenium-mediated reduction of α,β-epoxy ketones, α,β-epoxy esters, and their congeners to β-hydroxy carbonyl compounds: Novel methodologies for the synthesis of aldols and their analogues

Author keywords

[No Author keywords available]

Indexed keywords

KETOL;

EID: 0030841601     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00781-3     Document Type: Article
Times cited : (111)

References (46)
  • 2
    • 0002389988 scopus 로고
    • H. J. Reich, Acc. Chem. Res., 1979, 12, 22; D. L. J. Clive, Tetrahedron, 1978, 34, 1049; H. J. Reich, In "Oxidation in Organic Chemistry", W. Trahanovsky, Ed., Academic Press, New York, 1978, Part C, 1; D. Liotta, Acc. Chem. Res., 1984, 17, 28; C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis", Organic Chemistry Series, J. E. Baldwin, Ed., Pergamon Press, New York, 1986, Vol 4.
    • (1979) Acc. Chem. Res. , vol.12 , pp. 22
    • Reich, H.J.1
  • 3
    • 49349139760 scopus 로고
    • H. J. Reich, Acc. Chem. Res., 1979, 12, 22; D. L. J. Clive, Tetrahedron, 1978, 34, 1049; H. J. Reich, In "Oxidation in Organic Chemistry", W. Trahanovsky, Ed., Academic Press, New York, 1978, Part C, 1; D. Liotta, Acc. Chem. Res., 1984, 17, 28; C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis", Organic Chemistry Series, J. E. Baldwin, Ed., Pergamon Press, New York, 1986, Vol 4.
    • (1978) Tetrahedron , vol.34 , pp. 1049
    • Clive, D.L.J.1
  • 4
    • 0343652996 scopus 로고
    • W. Trahanovsky, Ed., Academic Press, New York
    • H. J. Reich, Acc. Chem. Res., 1979, 12, 22; D. L. J. Clive, Tetrahedron, 1978, 34, 1049; H. J. Reich, In "Oxidation in Organic Chemistry", W. Trahanovsky, Ed., Academic Press, New York, 1978, Part C, 1; D. Liotta, Acc. Chem. Res., 1984, 17, 28; C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis", Organic Chemistry Series, J. E. Baldwin, Ed., Pergamon Press, New York, 1986, Vol 4.
    • (1978) Oxidation in Organic Chemistry , Issue.PART C , pp. 1
    • Reich, H.J.1
  • 5
    • 0002756772 scopus 로고
    • H. J. Reich, Acc. Chem. Res., 1979, 12, 22; D. L. J. Clive, Tetrahedron, 1978, 34, 1049; H. J. Reich, In "Oxidation in Organic Chemistry", W. Trahanovsky, Ed., Academic Press, New York, 1978, Part C, 1; D. Liotta, Acc. Chem. Res., 1984, 17, 28; C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis", Organic Chemistry Series, J. E. Baldwin, Ed., Pergamon Press, New York, 1986, Vol 4.
    • (1984) Acc. Chem. Res. , vol.17 , pp. 28
    • Liotta, D.1
  • 6
    • 0004018071 scopus 로고
    • Organic Chemistry Series, J. E. Baldwin, Ed., Pergamon Press, New York
    • H. J. Reich, Acc. Chem. Res., 1979, 12, 22; D. L. J. Clive, Tetrahedron, 1978, 34, 1049; H. J. Reich, In "Oxidation in Organic Chemistry", W. Trahanovsky, Ed., Academic Press, New York, 1978, Part C, 1; D. Liotta, Acc. Chem. Res., 1984, 17, 28; C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis", Organic Chemistry Series, J. E. Baldwin, Ed., Pergamon Press, New York, 1986, Vol 4.
    • (1986) Selenium Reagents and Intermediates in Organic Synthesis , vol.4
    • Paulmier, C.1
  • 17
    • 0000145196 scopus 로고
    • T. Mukaiyama, Org. React., 1982, 28, 203; M. Braun, Angew. Chem. Int., Ed. Engl., 1987, 26, 24; I. Paterson, Chem. Ind., 1988, 390; E. R. Brukhant, J. J. Doney, G. A. Slough, J. M. Stack, C. H. Heathcock, and R. G. Bergman, Pure Appl. Chem., 1988, 60, 1; "Comprehensive Organic Synthesis", B. M. Trost, I. Fleming, Ed., Vol. 2, C. H. Heathcock, Ed., C. H. Heathcock, pp 133-238; B. M. Kim, S. F. Williams, and S. Masamune, pp 239-276.
    • (1982) Org. React. , vol.28 , pp. 203
    • Mukaiyama, T.1
  • 18
    • 84973329202 scopus 로고
    • T. Mukaiyama, Org. React., 1982, 28, 203; M. Braun, Angew. Chem. Int., Ed. Engl., 1987, 26, 24; I. Paterson, Chem. Ind., 1988, 390; E. R. Brukhant, J. J. Doney, G. A. Slough, J. M. Stack, C. H. Heathcock, and R. G. Bergman, Pure Appl. Chem., 1988, 60, 1; "Comprehensive Organic Synthesis", B. M. Trost, I. Fleming, Ed., Vol. 2, C. H. Heathcock, Ed., C. H. Heathcock, pp 133-238; B. M. Kim, S. F. Williams, and S. Masamune, pp 239-276.
    • (1987) Angew. Chem. Int., Ed. Engl. , vol.26 , pp. 24
    • Braun, M.1
  • 19
    • 0012392077 scopus 로고
    • T. Mukaiyama, Org. React., 1982, 28, 203; M. Braun, Angew. Chem. Int., Ed. Engl., 1987, 26, 24; I. Paterson, Chem. Ind., 1988, 390; E. R. Brukhant, J. J. Doney, G. A. Slough, J. M. Stack, C. H. Heathcock, and R. G. Bergman, Pure Appl. Chem., 1988, 60, 1; "Comprehensive Organic Synthesis", B. M. Trost, I. Fleming, Ed., Vol. 2, C. H. Heathcock, Ed., C. H. Heathcock, pp 133-238; B. M. Kim, S. F. Williams, and S. Masamune, pp 239-276.
    • (1988) Chem. Ind. , pp. 390
    • Paterson, I.1
  • 20
    • 0342859241 scopus 로고
    • T. Mukaiyama, Org. React., 1982, 28, 203; M. Braun, Angew. Chem. Int., Ed. Engl., 1987, 26, 24; I. Paterson, Chem. Ind., 1988, 390; E. R. Brukhant, J. J. Doney, G. A. Slough, J. M. Stack, C. H. Heathcock, and R. G. Bergman, Pure Appl. Chem., 1988, 60, 1; "Comprehensive Organic Synthesis", B. M. Trost, I. Fleming, Ed., Vol. 2, C. H. Heathcock, Ed., C. H. Heathcock, pp 133-238; B. M. Kim, S. F. Williams, and S. Masamune, pp 239-276.
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1
    • Brukhant, E.R.1    Doney, J.J.2    Slough, G.A.3    Stack, J.M.4    Heathcock, C.H.5    Bergman, R.G.6
  • 21
    • 0000851696 scopus 로고    scopus 로고
    • B. M. Trost, I. Fleming, Ed., C. H. Heathcock, Ed., C. H. Heathcock
    • T. Mukaiyama, Org. React., 1982, 28, 203; M. Braun, Angew. Chem. Int., Ed. Engl., 1987, 26, 24; I. Paterson, Chem. Ind., 1988, 390; E. R. Brukhant, J. J. Doney, G. A. Slough, J. M. Stack, C. H. Heathcock, and R. G. Bergman, Pure Appl. Chem., 1988, 60, 1; "Comprehensive Organic Synthesis", B. M. Trost, I. Fleming, Ed., Vol. 2, C. H. Heathcock, Ed., C. H. Heathcock, pp 133-238; B. M. Kim, S. F. Williams, and S. Masamune, pp 239-276.
    • Comprehensive Organic Synthesis , vol.2 , pp. 133-238
  • 22
    • 0343729816 scopus 로고    scopus 로고
    • T. Mukaiyama, Org. React., 1982, 28, 203; M. Braun, Angew. Chem. Int., Ed. Engl., 1987, 26, 24; I. Paterson, Chem. Ind., 1988, 390; E. R. Brukhant, J. J. Doney, G. A. Slough, J. M. Stack, C. H. Heathcock, and R. G. Bergman, Pure Appl. Chem., 1988, 60, 1; "Comprehensive Organic Synthesis", B. M. Trost, I. Fleming, Ed., Vol. 2, C. H. Heathcock, Ed., C. H. Heathcock, pp 133-238; B. M. Kim, S. F. Williams, and S. Masamune, pp 239-276.
    • Kim, B.M.1    Williams, S.F.2    Masamune, S.3
  • 29
    • 0015734087 scopus 로고
    • (g) Al(Hg): E. J. Corey, H. E. Ensley, J. Org. Chem., 1973, 38, 3187; G. R. Weihe and T. C. McMorris, J. Org. Chem., 1978, 43, 3942;
    • (1973) J. Org. Chem. , vol.38 , pp. 3187
    • Corey, E.J.1    Ensley, H.E.2
  • 30
    • 0018134889 scopus 로고
    • (g) Al(Hg): E. J. Corey, H. E. Ensley, J. Org. Chem., 1973, 38, 3187; G. R. Weihe and T. C. McMorris, J. Org. Chem., 1978, 43, 3942;
    • (1978) J. Org. Chem. , vol.43 , pp. 3942
    • Weihe, G.R.1    McMorris, T.C.2
  • 35
    • 0343294234 scopus 로고    scopus 로고
    • note
    • 2 in EtOH. (formula presented)
  • 40
    • 0024349560 scopus 로고
    • S. Takano, Y. Shimazaki, Y. Sekiguchi, and K. Ogasawara, Synthesis, 1989, 539; S. Takano, Y. Shimazaki, Y. Iwabuchi, and K. Ogasawara, Tetrahedron Lett., 1990, 31, 3619; N. Sakai and Y. Ohfune, Tetrahedron Lett., 1990, 31, 4151; S. Takano, M. Setoh, and K. Ogasawara, Tetrahedron: Asymmetry, 1992, 3, 533; N. Sakai and Y. Ohfune, J. Am. Chem. Soc., 1992, 114, 998; S. Takano, T. Kamikubo, T. Sugihara, M. Suzuki, and K. Ogasawara, Tetrahedron: Asymmetry, 1993, 4, 201.
    • (1989) Synthesis , pp. 539
    • Takano, S.1    Shimazaki, Y.2    Sekiguchi, Y.3    Ogasawara, K.4
  • 41
    • 0025352649 scopus 로고
    • S. Takano, Y. Shimazaki, Y. Sekiguchi, and K. Ogasawara, Synthesis, 1989, 539; S. Takano, Y. Shimazaki, Y. Iwabuchi, and K. Ogasawara, Tetrahedron Lett., 1990, 31, 3619; N. Sakai and Y. Ohfune, Tetrahedron Lett., 1990, 31, 4151; S. Takano, M. Setoh, and K. Ogasawara, Tetrahedron: Asymmetry, 1992, 3, 533; N. Sakai and Y. Ohfune, J. Am. Chem. Soc., 1992, 114, 998; S. Takano, T. Kamikubo, T. Sugihara, M. Suzuki, and K. Ogasawara, Tetrahedron: Asymmetry, 1993, 4, 201.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3619
    • Takano, S.1    Shimazaki, Y.2    Iwabuchi, Y.3    Ogasawara, K.4
  • 42
    • 0025364258 scopus 로고
    • S. Takano, Y. Shimazaki, Y. Sekiguchi, and K. Ogasawara, Synthesis, 1989, 539; S. Takano, Y. Shimazaki, Y. Iwabuchi, and K. Ogasawara, Tetrahedron Lett., 1990, 31, 3619; N. Sakai and Y. Ohfune, Tetrahedron Lett., 1990, 31, 4151; S. Takano, M. Setoh, and K. Ogasawara, Tetrahedron: Asymmetry, 1992, 3, 533; N. Sakai and Y. Ohfune, J. Am. Chem. Soc., 1992, 114, 998; S. Takano, T. Kamikubo, T. Sugihara, M. Suzuki, and K. Ogasawara, Tetrahedron: Asymmetry, 1993, 4, 201.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4151
    • Sakai, N.1    Ohfune, Y.2
  • 43
    • 0026578717 scopus 로고
    • S. Takano, Y. Shimazaki, Y. Sekiguchi, and K. Ogasawara, Synthesis, 1989, 539; S. Takano, Y. Shimazaki, Y. Iwabuchi, and K. Ogasawara, Tetrahedron Lett., 1990, 31, 3619; N. Sakai and Y. Ohfune, Tetrahedron Lett., 1990, 31, 4151; S. Takano, M. Setoh, and K. Ogasawara, Tetrahedron: Asymmetry, 1992, 3, 533; N. Sakai and Y. Ohfune, J. Am. Chem. Soc., 1992, 114, 998; S. Takano, T. Kamikubo, T. Sugihara, M. Suzuki, and K. Ogasawara, Tetrahedron: Asymmetry, 1993, 4, 201.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 533
    • Takano, S.1    Setoh, M.2    Ogasawara, K.3
  • 44
    • 0026567703 scopus 로고
    • S. Takano, Y. Shimazaki, Y. Sekiguchi, and K. Ogasawara, Synthesis, 1989, 539; S. Takano, Y. Shimazaki, Y. Iwabuchi, and K. Ogasawara, Tetrahedron Lett., 1990, 31, 3619; N. Sakai and Y. Ohfune, Tetrahedron Lett., 1990, 31, 4151; S. Takano, M. Setoh, and K. Ogasawara, Tetrahedron: Asymmetry, 1992, 3, 533; N. Sakai and Y. Ohfune, J. Am. Chem. Soc., 1992, 114, 998; S. Takano, T. Kamikubo, T. Sugihara, M. Suzuki, and K. Ogasawara, Tetrahedron: Asymmetry, 1993, 4, 201.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 998
    • Sakai, N.1    Ohfune, Y.2
  • 45
    • 0027523478 scopus 로고
    • S. Takano, Y. Shimazaki, Y. Sekiguchi, and K. Ogasawara, Synthesis, 1989, 539; S. Takano, Y. Shimazaki, Y. Iwabuchi, and K. Ogasawara, Tetrahedron Lett., 1990, 31, 3619; N. Sakai and Y. Ohfune, Tetrahedron Lett., 1990, 31, 4151; S. Takano, M. Setoh, and K. Ogasawara, Tetrahedron: Asymmetry, 1992, 3, 533; N. Sakai and Y. Ohfune, J. Am. Chem. Soc., 1992, 114, 998; S. Takano, T. Kamikubo, T. Sugihara, M. Suzuki, and K. Ogasawara, Tetrahedron: Asymmetry, 1993, 4, 201.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 201
    • Takano, S.1    Kamikubo, T.2    Sugihara, T.3    Suzuki, M.4    Ogasawara, K.5
  • 46
    • 0342859236 scopus 로고    scopus 로고
    • note
    • Ordinary EtOH is sufficient for use instead of absolute EtOH employed in the original paper, ref. 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.