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Stereoselective Synthesis of (Z)-2-Acylamido-4-phenylcrotonates

Stereoselective Synthesis of (Z)-2-Acylamido-4-phenylcrotonates
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摘要 Two practical methods for highly stereoselective synthesis of (Z)-2-acylamido-4-phenylcrotonates 2a similar to b have been developed. The key step in the first route was how to control the acid-catalyzed isomerization of condensation mixtures of alpha-keto ester 5 with carbomite. In the second route the key step was reduction of oxime 8, derived from alpha-keto ester 5, with iron powder in the presence of acetic anhydride. Two practical methods for highly stereoselective synthesis of (Z)-2-acylamido-4-phenylcrotonates 2a similar to b have been developed. The key step in the first route was how to control the acid-catalyzed isomerization of condensation mixtures of alpha-keto ester 5 with carbomite. In the second route the key step was reduction of oxime 8, derived from alpha-keto ester 5, with iron powder in the presence of acetic anhydride.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2000年第7期567-570,共4页 中国化学快报(英文版)
关键词 (Z)-alpha beta-dehydroamino acids stereoselective synthesis E -> Z isomerization Fe/Ac2O reduction of oxime (Z)-alpha,beta-dehydroamino acids stereoselective synthesis E -> Z isomerization Fe/Ac2O reduction of oxime
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参考文献3

  • 1G. A. Olah,R. D. Porter,J Am. Chemical Society Reviews . 1971
  • 2M. J. Burk,G. Casy,N. B. Johsons,J Org. Chemtracts . 1998
  • 3G. Zhu,A. L. Casalnuovo,X. M. Zhang,J.Org. Chemtracts . 1998

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