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Volumn 56, Issue 9, 2000, Pages 1149-1163

Reactions of epoxides with ester, ketone and amide enolates

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; EPOXIDE; ESTER; KETONE; LACTONE;

EID: 0034712223     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01074-1     Document Type: Review
Times cited : (104)

References (85)
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    • Tu, Y.; Wang, Z. -X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806; Wang, Z. -X.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62, 2328.
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    • Tu, Y.1    Wang, Z.-X.2    Shi, Y.3
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    • Wang, Z.-X.; Tu, Y.; Frohn, M.; Shi, Y.
    • Tu, Y.; Wang, Z. -X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806; Wang, Z. -X.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62, 2328.
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    • Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391; Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288.
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  • 19
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    • Catalytic Asymmetric Epoxidation of Allylic Alcohols
    • I. Ojima. New York: VCH
    • Sharpless K.B., Johnson R.A. Catalytic Asymmetric Epoxidation of Allylic Alcohols. Ojima I. Catalytic Asymmetric Synthesis. 1993;103 VCH, New York.
    • (1993) Catalytic Asymmetric Synthesis , pp. 103
    • Sharpless, K.B.1    Johnson, R.A.2
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    • Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins
    • I. Ojima. New York: VCH
    • Jacobson E.N. Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins. Ojima I. Catalytic Asymmetric Synthesis. 1993;159 VCH, New York.
    • (1993) Catalytic Asymmetric Synthesis , pp. 159
    • Jacobson, E.N.1
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    • For a general review, see
    • For a general review, see Smith, J. G. Synthesis 1984, 629.
    • (1984) Synthesis , pp. 629
    • Smith, J.G.1
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    • 28 (this work will be published under separate cover). Lactone 22e as made in 96% ee, as shown by chiral GC (β-cyclodextrin column). 22d was made in an 86:14 enantiomeric ratio, exactly the same R:S ratio as the starting epoxide.
    • 28 (this work will be published under separate cover). Lactone 22e as made in 96% ee, as shown by chiral GC (β-cyclodextrin column). 22d was made in an 86:14 enantiomeric ratio, exactly the same R:S ratio as the starting epoxide.
  • 67
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    • No other workers did similar work and cited Crotti, as evidenced by a recent SCI search.
    • No other workers did similar work and cited Crotti, as evidenced by a recent SCI search.
  • 74
    • 0031955351 scopus 로고    scopus 로고
    • Nitriles also form lithium enolates that react directly with epoxides. Their chemistry is very straightforward, and it will not be discussed. For representative reports, see and references therein
    • Nitriles also form lithium enolates that react directly with epoxides. Their chemistry is very straightforward, and it will not be discussed. For representative reports, see Taylor, S. K.; DeYoung, D.; Simons, L. J.; Vyvyan, J.; R.; Wemple, M. A.; Wood, N.K. Synth. Commun. 1998, 28, 1691 and references therein.
    • (1998) Synth. Commun. , vol.28 , pp. 1691
    • Taylor, S.K.1    Deyoung, D.2    Simons, L.J.3    Vyvyan, J.R.4    Wemple, M.A.5    Wood, N.K.6
  • 75
    • 0343375537 scopus 로고    scopus 로고
    • A thorough search was complicated because some workers did not cite key references
    • A thorough search was complicated because some workers did not cite key references.
  • 79
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    • According to the article, neutral hydrolysis was allowed to occur by diluting the reaction mixture with THF and allowing it to agitate overnight under ambient conditions.
    • According to the article, neutral hydrolysis was allowed to occur by diluting the reaction mixture with THF and allowing it to agitate overnight under ambient conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.