DiastereoselectiveandEnantioselectiveSynthesisof(1S,2S)-2-Ethyl-1-aminocyclopropaneCarboxylicAcid

Diastereoselective and Enantioselective Synthesis of (1S, 2S)-2- Ethyl-1-aminocyclopropane Carboxylic Acid

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摘要 Pd(0) Complex prepared from Pd(dba)(2) and chiral quinolinyl-oxazoline ligand can catalyze alkylation and cyclization reaction of 1, 4-dichlorobut-2-ene 1 with anion of N-(diphenylmethylene)amino acetonitrile 2 to provide (E)-2-ethenyl-1-N-(diphenylmethylene) amino cyclopropane carbonitrile 3 with 100% de and 20% cc. Reduction of (E)-3 by diimide followed by acidic hydrolysis afforded (1S, 2S)-2-ethyl-1-aminocyclopropanecarboxylic acid 9, a natural product coronamic acid. Pd(0) Complex prepared from Pd(dba)(2) and chiral quinolinyl-oxazoline ligand can catalyze alkylation and cyclization reaction of 1, 4-dichlorobut-2-ene 1 with anion of N-(diphenylmethylene)amino acetonitrile 2 to provide (E)-2-ethenyl-1-N-(diphenylmethylene) amino cyclopropane carbonitrile 3 with 100% de and 20% cc. Reduction of (E)-3 by diimide followed by acidic hydrolysis afforded (1S, 2S)-2-ethyl-1-aminocyclopropanecarboxylic acid 9, a natural product coronamic acid.

作者 Yi Bo ZHOU Jun An MA Li Xin WANG Qi Lin ZHOU

机构地区 State Key Laboratoratory and Institute of Elemento-Organic Chemistry

出处《Chinese Chemical Letters》 SCIE CAS CSCD 2002年第10期939-941,共3页 中国化学快报(英文版)

基金 the National Natural Science Foundation of China the Major State Basic Research Development Program(grant No.G2000077506) the Ministry of Education of China for the financial support.

关键词 Chiral Pd catalyst quinolinyl-oxazoline cyclopropanecarboxylic acid. chiral Pd catalyst quinolinyl-oxazoline cyclopropanecarboxylic acid

分类号 O643.3 [理学—物理化学]

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Chinese Chemical Letters

2002年第10期

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DiastereoselectiveandEnantioselectiveSynthesisof(1S,2S)-2-Ethyl-1-aminocyclopropaneCarboxylicAcid

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