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Volumn 64, Issue 22, 1999, Pages 8193-8200

Highly diastereoselective aldol reactions with camphor-based acetate enolate equivalents

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CAMPHOR;

EID: 0033615583     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990865z     Document Type: Article
Times cited : (45)

References (109)
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    • (g) Braun, M. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. E21/3, p 1603.
    • (1996) Stereoselective Synthesis (Houben-Weyl) , vol.E21-3 , pp. 1603
    • Braun, M.1
  • 11
    • 0030445798 scopus 로고    scopus 로고
    • For recent reviews on catalytic enantioselective aldol additions, see: (a) Mukaiyama, T. Aldrichim. Acta 1996, 29, 59.
    • (1996) Aldrichim. Acta , vol.29 , pp. 59
    • Mukaiyama, T.1
  • 17
    • 0038468227 scopus 로고    scopus 로고
    • Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. For recent examples of chiral auxiliary methodology in aldol reactions, see: From oxazinone-imide enolates.
    • (1996) Chem. Rev. , vol.96 , pp. 835
    • Ager, D.J.1    Prakash, I.2    Schaad, D.R.3
  • 67
    • 0345023232 scopus 로고    scopus 로고
    • Bal, B.; Buse, C. T.; Smith, K.; Heathcock, C. H. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. 7, p 185.
    • Collect. , vol.7 , pp. 185
  • 68
    • 0345454398 scopus 로고    scopus 로고
    • For detailed information on this topic, see: (a) ref 1f,g
    • For detailed information on this topic, see: (a) ref 1f,g.
  • 70
    • 0001088334 scopus 로고
    • V. Snieckus, Ed.; Jai Press: London
    • Braun, M. In Advances in Carbanion Chemistry; V. Snieckus, Ed.; Jai Press: London, 1992; Vol. 1, p 177. For recent examples on acetate imide or thioimide enolate, see:
    • (1992) Advances in Carbanion Chemistry , vol.1 , pp. 177
    • Braun, M.1
  • 76
    • 0000634244 scopus 로고    scopus 로고
    • Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. For a recent example on virtually complete asymmetric induction with a methyl ketone via SAEP-hydrazone, see:
    • (1997) J. Org. Chem. , vol.62 , pp. 6397
    • Bond, S.1    Perlmutter, P.2
  • 81
    • 0344160595 scopus 로고    scopus 로고
    • For catalytic asymmetric aldol reactions solving this problem, see: (a) Reference 36
    • For catalytic asymmetric aldol reactions solving this problem, see: (a) Reference 36.
  • 95
    • 0345454395 scopus 로고    scopus 로고
    • For these reactions we have systematically employed a 6-fold excess of LiCl. Nonetheless, we have found that as little as 3-fold excess of LiCl, but not less, provides the same effect on diastereoselectivity
    • For these reactions we have systematically employed a 6-fold excess of LiCl. Nonetheless, we have found that as little as 3-fold excess of LiCl, but not less, provides the same effect on diastereoselectivity.
  • 97
    • 0001346069 scopus 로고
    • For transition structures involved in aldol reactions of lithium enolates, see: Li, Y.; Paddon-Row, M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 481.
    • (1990) J. Org. Chem. , vol.55 , pp. 481
    • Li, Y.1    Paddon-Row, M.N.2    Houk, K.N.3
  • 102
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    • note
    • Crystallographic data (excluding structure factors) for the structure of 26 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101850. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax (+44) 1223 336-033; email deposit@ccdc.cam.ac.uk). For Crystallographic data of the structure 3, 51, and 20, see ref 10.
  • 104
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    • Collect. , vol.8 , pp. 391
  • 106
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    • Fischer, N.; Opitz, G. Organic Syntheses: Wiley: New York, 1973; Collect. Vol. 5, p 877.
    • Collect. , vol.5 , pp. 877


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.