TOTALLY STEREOCONTROLLED NITRONE-KETENE ACETAL BASED SYNTHESIS OF (2S,3S)-N-BENZOYL-PHENYLISOSERINE AND N-BOC-PHENYLISOSERINE

Authors
JOST S GIMBERT Y GREENE AE FOTIADU F
Citation
S. Jost et al., TOTALLY STEREOCONTROLLED NITRONE-KETENE ACETAL BASED SYNTHESIS OF (2S,3S)-N-BENZOYL-PHENYLISOSERINE AND N-BOC-PHENYLISOSERINE, Journal of organic chemistry, 62(19), 1997, pp. 6672-6677
Citations number
51
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
19
Year of publication
1997
Pages
6672 - 6677
Database
ISI
SICI code
0022-3263(1997)62:19<6672:TSNABS>2.0.ZU;2-G
Abstract
A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N -benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceed s in up to 59% overall yield and requires only three operations from t he starting nitrones.