引用本文:
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.
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.
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.
Diastereoselective and Enantioselective Synthesis of (1S,2S)-2-Ethyl-1-aminocyclopropane Carboxylic Acid
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% 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.
English
Diastereoselective and Enantioselective Synthesis of (1S,2S)-2-Ethyl-1-aminocyclopropane Carboxylic Acid
Abstract:
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.
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Key words:
- Chiral Pd catalyst
- / quinolinyl-oxazoline
- / cyclopropanecarboxylic acid
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