Citation: Yi Nong XIE, Fan Min FU, Ai Qiao MI, Yao Zhong JIANG. Stereoselective Synthesis of (Z)-2-Acylamido-4-phenylcrotonates[J]. Chinese Chemical Letters, ;2000, 11(7): 567-570. shu

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

Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041

Received Date: 2 January 2000

Fund Project: This project was supported by the National Natural Science Foundation of China. No.29790124

Two practical methods for highly stereoselective synthesis of (Z)-2-acylamido-4-phenylcrotonates 2a~b have been developed. The key step in the first route was how to control the acid-catalyzed isomerization of condensation mixtures of α-keto ester 5 with carbomite. In the second route the key step was reduction of oxime 8, derived from α-keto ester 5, with iron powder in the presence of acetic anhydride.
- (Z)-α,β-Dehydroamino acids,
- stereoselective synthesis,
- E→Z isomerization,
- Fe/Ac₂O reduction of oxime
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