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Diastereoselective synthesis of (1S)-trans-cyclopropane-1,2-dicarboxylic acid derivatives using 1,2;4,5-di-O-isopropylidene-D-fructopyranose as the chiral auxiliary

Yun-Feng Li, Xiang-Bao Meng*, Qing Li, Zhong-Jun Li*
  

  1. The State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
  • Received:2008-11-17 Revised:2009-02-10 Online:2009-03-15 Published:2009-03-15
  • Contact: Xiang-Bao Meng*, Zhong-Jun Li*

Abstract:

A new procedure for the highly diastereoselective synthesis of (1S)-trans-cyclopropane derivatives using a fructose derivative as the chiral auxiliary was developed. Chloroacetylated 1,2;4,5-di-O-isopropylidene-D-fructopyranose was reacted with a tertiary amine to form the ammonium salt, which was treated with cesium carbonate to give the cyclopropane derivative through ylide intermediate. The described procedure provides an efficient method to synthesize optically pure di- or poly-substituded cyclopropanes.

Key words: Chiral auxiliary, Chiral auxiliary, Sugar, Sugar, Asymmetric synthesis, Asymmetric synthesis, Cyclopropanation, Cyclopropanation

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