Synthesis of 3-Bicyclo[3.3.0]octene Derivatives Containing Multiple Chiral Centers

Abstract

Abstract: 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-bicy-clo [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]_D²⁰, UV, IR,¹HNMR, ¹³CNMR, 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.

Key words: Tandem reaction, Asymmetric Michael addition/intramolecular nucleophilic sub-stitution, Crystal structure, Chiral 3-bicyclo[3.3.0]octene compound

CLC Number:

O621

TrendMD:

HUANG Hui, CHEN Qing-Hua. Synthesis of 3-Bicyclo[3.3.0]octene Derivatives Containing Multiple Chiral Centers[J]. Chem. J. Chinese Universities, 1999, 20(9): 1384.

References

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