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An enantioselective synthesis of (+)-polyoxamic acid via phase-transfer catalytic conjugate addition and asymmetric dihydroxylation.

Authors :
Lee YJ
Park Y
Kim MH
Jew SS
Park HG
Source :
The Journal of organic chemistry [J Org Chem] 2011 Jan 21; Vol. 76 (2), pp. 740-3. Date of Electronic Publication: 2010 Dec 30.
Publication Year :
2011

Abstract

A new enantioselective synthetic method of (+)-polyoxamic acid is reported. (+)-Polyoxamic acid could be obtained in 7 steps with 46% overall yield from diphenylmethyl-glycineimine tert-butyl ester via an enantioselective phase-transfer conjugate addition (99% yield, 96% ee) and an asymmetric dihydroxylation (98% yield, 94% de) as the key reactions.

Details

Language :
English
ISSN :
1520-6904
Volume :
76
Issue :
2
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
21192648
Full Text :
https://doi.org/10.1021/jo102272h