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

doi:10.1002/chir.20070

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

Chirality. 2004 Oct;16(8):516-9. doi: 10.1002/chir.20070.

Authors

Zhenjun Du¹, Zhenliang Chen, Zhiyong Chen, Xiaoqi Yu, WenHao Hu

Affiliation

¹ Department of Chemistry Sichuan University, Chengdu, P. R. China.

PMID: 15290686
DOI: 10.1002/chir.20070

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetamides / chemistry*
Azo Compounds / chemistry*
Catalysis
Molecular Structure
Organometallic Compounds / chemistry*
Stereoisomerism
gamma-Aminobutyric Acid / analogs & derivatives*
gamma-Aminobutyric Acid / chemical synthesis*
gamma-Aminobutyric Acid / chemistry*

Substances

Acetamides
Azo Compounds
N-(2-benzyloxyethyl)-N-(tert-butyl)diazoacetamide
Organometallic Compounds
Rh(2)(MEOX)(4)
4-amino-3-hydroxybutyric acid
gamma-Aminobutyric Acid