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Volumn 3, Issue 26, 2001, Pages 4251-4254

Enantioselective 1,4-addition of unmodified ketone catalyzed by a bimetallic Zn-Zn-linked-binol complex

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ARTICLE;

EID: 0001313530     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016981h     Document Type: Article
Times cited : (74)

References (59)
  • 3
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    • (a) Trost, B. M. Science 1991, 254, 1471.
    • (1991) Science , vol.254 , pp. 1471
    • Trost, B.M.1
  • 19
    • 0034596299 scopus 로고    scopus 로고
    • Unmodified α-hydroxyketones as donors: (h) The use of α-hydroxyketones with chemical catalysts has been pioneered by List et al.: Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7386
    • Notz, W.1    List, B.2
  • 28
    • 0035126119 scopus 로고    scopus 로고
    • For recent reviews on the catalytic asymmetric 1,4-addition reactions, see: (a) Krause, N.; Hoffmann-Röder, A. Synthesis, 2001, 171.
    • (2001) Synthesis , pp. 171
    • Krause, N.1    Hoffmann-Röder, A.2
  • 30
    • 0002436782 scopus 로고
    • Excellent catalytic asymmetric 1,4-addition reactions with latent enolates, such as enol silyl ether, are established (>90% ee), although those reactions require stoichiometric amounts of reagents to prepare latent enolates. For recent representative examples, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem Lett. 1994, 97.
    • (1994) Chem Lett. , pp. 97
    • Kobayashi, S.1    Suda, S.2    Yamada, M.3    Mukaiyama, T.4
  • 35
    • 0343967492 scopus 로고    scopus 로고
    • For leading references on catalytic asymmetric 1,4-addition reactions of other carbon nucleophiles, see malonates: (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520.
    • (1996) J. Org. Chem. , vol.61 , pp. 3520
    • Yamaguchi, M.1    Shiraishi, T.2    Hirama, M.3
  • 39
    • 0034975355 scopus 로고    scopus 로고
    • See also, ref 8, 10b and references therein
    • B reagents: (j) Hayashi, T. Synlett 2001, 879. See also, ref 8, 10b and references therein.
    • (2001) Synlett , pp. 879
    • Hayashi, T.1
  • 44
    • 0041718598 scopus 로고    scopus 로고
    • note
    • For other chiral bimetallic Zn catalysts, see refs 4b, 4e, 4i and references therein.
  • 48
    • 0041718595 scopus 로고    scopus 로고
    • note
    • 4. The solvent was removed under reduced pressure, and the residue was purified by flash silica gel column chromatography (hexane/acetone 6/1) to afford 4a (272.5 mg. 0.829 mmol, 83%).
  • 50
    • 0041718596 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 51
    • 33947085552 scopus 로고
    • The absolute configurations of 4c and 6a were determined by Mosher's method. Those of others were temporarily determined by analogy, (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 512
    • Dale, J.A.1    Mosher, H.S.2
  • 52
    • 0043221179 scopus 로고    scopus 로고
    • note
    • The chelate complex formation through the coordination of 2′-methoxy group was essential to achieve high ee in the direct aldol reaction of 2 and aldehydes. See ref 3h.
  • 53
    • 0041718597 scopus 로고    scopus 로고
    • note
    • The benzoate 7c was prepared by treating 4c with benzoyl chloride. See Supporting Information.
  • 58
    • 0042218882 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of isolated product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.