Citation: Yi Bo ZHOU, Jun An MA, Li Xin WANG, Qi Lin ZHOU. Diastereoselective and Enantioselective Synthesis of (1S,2S)-2-Ethyl-1-aminocyclopropane Carboxylic Acid[J]. Chinese Chemical Letters, ;2002, 13(10): 939-941. shu

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

State Key Laboratoratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received Date: 3 December 2001

Fund Project: We thank the National Natural Science Foundation of China, the Major Slate Basic Research Development Program (grant No.G2000077506), the Ministry of Education of China for the financial support.

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% ee. Reduction of (E)-3 by diimide followed by acidic hydrolysis afforded (1S, 2S)-2-ethyl-1-aminocyclopropanecarboxylic acid 9, a natural product coronamic acid.
- Chiral Pd catalyst,
- quinolinyl-oxazoline,
- cyclopropanecarboxylic acid
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