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Volumn 37, Issue 38, 1996, Pages 6931-6934

New chiral acetate imide enolate for stereoselective aldol reactions

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

EID: 0030590405     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01520-1     Document Type: Article
Times cited : (17)

References (39)
  • 1
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    • Eds.: Trost, B.M.; Fleming, I., Pergamon Press, Oxford, Ed.: Heathcock, C.H.
    • 1. Comprehensive Organic Chemistry, (Eds.: Trost, B.M.; Fleming, I.), Pergamon Press, Oxford, 1991, Vol. 2, (Ed.: Heathcock, C.H.):
    • (1991) Comprehensive Organic Chemistry , vol.2
  • 2
    • 85030274866 scopus 로고    scopus 로고
    • chapter 1.5, 133
    • (a) Heathcock, C.H., chapter 1.5, pp 133; chapter 1.6 pp. 181;
    • Heathcock, C.H.1
  • 3
    • 85030272151 scopus 로고    scopus 로고
    • chapter 1.6
    • (a) Heathcock, C.H., chapter 1.5, pp 133; chapter 1.6 pp. 181;
  • 5
    • 85030270774 scopus 로고    scopus 로고
    • chapter 1.9
    • (c) Paterson, I., chapter 1.9, pp. 301.
    • Paterson, I.1
  • 8
    • 0002652021 scopus 로고
    • Ed.: Morrison, J.D. Academic Press, New York
    • 3 Evans, D.A. in Asymmetric Synthesis (Ed.: Morrison, J.D.) Academic Press, New York, 1984, Vol. 3, p.1.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 1
    • Evans, D.A.1
  • 10
    • 0038736789 scopus 로고
    • 4 Oppolzer, W.; Bragg, J.; Walter, E. J. Am. Chem. Soc., 1990, 112, 2767. For a review, see: Oppolzer, W. Tetrahedron, 1987, 43, 1969.
    • (1987) Tetrahedron , vol.43 , pp. 1969
    • Oppolzer, W.1
  • 13
    • 0026579593 scopus 로고
    • For a detailed information on aldol reactions using α-unsubstituted enolates, see
    • 6. For a relevant example using a diastereoselective Mukaiyama aldol reaction, see: Oppolzer, W.; Starkemann, C. Tetrahedron Lett., 1992, 33, 2439. For a detailed information on aldol reactions using α-unsubstituted enolates, see:
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2439
    • Oppolzer, W.1    Starkemann, C.2
  • 15
    • 0001088334 scopus 로고
    • Ed.: Snieckus, V. Jai Press, London
    • (b) Braun, M. in Advances in Carbanion Chemistry (Ed.: Snieckus, V.) Jai Press, London, Vol. 1, 1992, p. 177.
    • (1992) Advances in Carbanion Chemistry , vol.1 , pp. 177
    • Braun, M.1
  • 23
    • 84985633277 scopus 로고
    • 11. Normally, lithium enolates of chiral acetates require transmetalation to achieve good diastereoselectivity, otherwise lower levels of asymmetric induction are often observed. For example, see: (a) Helmchen, G.; Leikauf, U.; Taufer-Knopfel, I. Angew. Chem. Int. Ed. Engl., 1985, 24, 874;
    • (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 874
    • Helmchen, G.1    Leikauf, U.2    Taufer-Knopfel, I.3
  • 34
    • 85030277896 scopus 로고    scopus 로고
    • note
    • 8b.
  • 35
    • 33751385708 scopus 로고
    • and references cited therein
    • 17. During the course of our investigations an example of such a reversal, unnoticed by the authors, has appeared (ref. 12). For a detailed discussion on this topic for aldol reactions with α-substituted enolates, see: (a) Pridgen, L.N.; Abdel-Magid, A.F.; Lantos, I.; Shilcrat, S.; Eggleston, D.S. J. Org. Chem., 1993, 58, 5107, and references cited therein.
    • (1993) J. Org. Chem. , vol.58 , pp. 5107
    • Pridgen, L.N.1    Abdel-Magid, A.F.2    Lantos, I.3    Shilcrat, S.4    Eggleston, D.S.5
  • 36
    • 85030269627 scopus 로고    scopus 로고
    • note
    • 18. This uniform behaviour has been shown by different metal enolates, as reported in ref. 7, 8b, 9, 10, 11a-c and 13.
  • 39
    • 85030269056 scopus 로고    scopus 로고
    • note
    • 21. The structure of 5g and 10 was unequivocally confirmed by X-ray crystallographic analysis. The X-ray data have been deposited at Cambridge Crystallographic Data Center.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.