Title of article :
Diastereoselective Horner-Wadsworth-Emmons Reaction for the Synthesis of Tetrasubstituted Alkenes with an Axis of Chirality
Author/Authors :
Sano, Shigeki The University of Tokushima - Graduate School of Pharmaceutical Sciences, Japan , Abe, Shinobu The University of Tokushima - Graduate School of Pharmaceutical Sciences, Japan , Azetsu, Tomohiro The University of Tokushima - Graduate School of Pharmaceutical Sciences, Japan , Nakao, Michiyasu The University of Tokushima - Graduate School of Pharmaceutical Sciences, Japan , Shiro, Motoo Rigaku Corporation, Japan , Nagao, Yoshimitsu The University of Tokushima - Graduate School of Pharmaceutical Sciences, Japan
Abstract :
An asymmetric Horner-Wadsworth-Emmons (HWE) reaction of s-symmetric 4-methylcyclohexanone(6c) and a novel HWE reagent 4a bearing O-benzylisomannide was investigated by employing Sn(OSO2CF3)2and N-ethylpiperidine.As a result, α-methyl-α,β-unsaturated ester 7c, a tetrasubstituted alkene with an axis of chirality, was obtained in 99% de.
Keywords :
Axis of chirality , Horner , Wadsworth , Emmons reaction , asymmetric synthesis , isomannide , tetrasubstitutedalkenes , diastereoselective
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
