Chirality 2004-10-01

Dirhodium-catalyzed enantioselective C-H insertion of N-(2-benzyloxyethyl)-N-(tert-butyl)diazoacetamide and its application for the synthesis of chiral GABOB.

Zhenjun Du, Zhenliang Chen, Zhiyong Chen, Xiaoqi Yu, WenHao Hu

Index: Chirality 16(8) , 516-9, (2004)

Full Text: HTML

Abstract

Rh(2)(4S-MEOX)(4) and ethereal solvent are the best catalytic system for the enantioselective intramolecular C-H insertion of N-(2-benzyloxyethyl)-N-(tert-butyl)diazoacetamide 2. The highest enantiomeric excess obtained was 91%. A new route for the asymmetric synthesis of gamma-amino-beta-hydroxybutyric acid (GABOB) has been developed.