Synthesis of 3-Bicyclo[3.3.0]octene Derivatives Containing Multiple Chiral Centers
HUANG Hui; CHEN Qing-Hua(Department of Chemistry, Betjing Normal University, Beijing 100875, China)
The tandem asymmetric Michael addition/intramolecular nucleophilic substitution of the novel chiral source, 3-bromo-5- (1-menthyloxy)-2 (5H)-furanone (1) with some carbon nucleophiles has been investigated. The asymmetric reaction can yield optically pure 3-bicyclo [3.3.0]octene derivatives containing two novel stereogenic chiral centers. The chemical structure and configuration of these 3-bicyclo[3.3.0]octene compounds were identified on the basis of their elemental analytical data and spectroscopic data, such as[α] , UV, IR,1H NMR, 13C NMR, MS and X-ray crystallography.This asymmetric reaction can provide an important strategy in synthesis of some optically pure 3-bicyclo[3. 3. 0]octene compounds and some biologically active molecules.