CJCU

Chem. J. Chinese Universities ›› 1998, Vol. 19 ›› Issue (8): 1256.

• Articles • Previous Articles     Next Articles

Asymmetric Synthesis of Optically Active 2-Ethyl-1-Amino-cyclopropanecarboxylic Acid via Pianone Ketimine

SU Gui-Fa1, Philippe Dorizon2, Jean Ollivier2, Jacques Salaün2   

  1. 1. Department of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin, 541004;
    2. Laboratoire des Carbocycles, ICMO, Bat 420, Universitéde Paris-Sud, 91405, Orsay Cédéx, France
  • Received:1997-06-07 Online:1998-08-24 Published:1998-08-24

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Abstract: Optically active cyclopropanes(4) were obtained by using 2-hydroxypinan-3-one 1 as a chiral auxiliary, condensed with aminoacetonitrile to form a chiral ketimine 2 followed by Pd(0) catalyzed tandem alkylation and SN'cyclisation of 1,4-dichlorobut-2-ene 3 with chiral ketimine 2. The yields are 69% and the diastereoselectivities of reaction are 100%. After the selective reduction of ethenyl group of 4, then by simple acid hydrolysis, optically active-2-ethyl 1-amino-cyclopropanecarboxylic acid 6 could be obtained, the e.e. value of 6 is 33%.

Key words: 2-Hydroxypinan-3-one, 1,4-Dichlorobut-2-ene, Chiral imine, Tandem reaction, 2-Ethyl-1-mino-cyclopropanecarboxylic acid

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