Dirhodium-catalyzed enantioselective C-H insertion of N-(2-benzyloxyethyl)-N-(tert-butyl)diazoacetamide and its application for the synthesis of chiral GABOB.
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.
Department of Chemistry Sichuan University, Chengdu, P. R. China.
Zhenjun
Z
Du
Zhenliang
Z
Chen
Zhiyong
Z
Chen
Xiaoqi
X
Yu
WenHao
W
Hu
D000081:Acetamides / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
D000081:Acetamides; D001391:Azo Compounds; C492683:N-(2-benzyloxyethyl)-N-(tert-butyl)diazoacetamide; D009942:Organometallic Compounds; C492682:Rh(2)(MEOX)(4); C004480:4-amino-3-hydroxybutyric acid; D005680:gamma-Aminobutyric Acid