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

Rh2(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 γ-amino-β-hydroxybutyric acid (GABOB) has been developed. Chirality 16:516–519, 2004. © 2004 Wiley-Liss, Inc.