APPLICATION OF ENANTIOPURE TEMPLATED AZOMETHINE YLIDS TO BETA-HYDROXY-ALPHA-AMINO ACID SYNTHESIS

Authors
ALKER D HAMBLETT G HARWOOD LM ROBERTSON SM WATKIN DJ WILLIAMS CE
Citation
D. Alker et al., APPLICATION OF ENANTIOPURE TEMPLATED AZOMETHINE YLIDS TO BETA-HYDROXY-ALPHA-AMINO ACID SYNTHESIS, Tetrahedron, 54(22), 1998, pp. 6089-6098
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
22
Year of publication
1998
Pages
6089 - 6098
Database
ISI
SICI code
0040-4020(1998)54:22<6089:AOETAY>2.0.ZU;2-E
Abstract
Chiral stabilised azomethine ylids derived from the reaction of (5S)-5 -phenylmorpholin-2-one (1) with aldehydes undergo efficient and highly diastereocontrolled cycloaddition with a second molecule of aldehyde to furnish products (2) which may be converted into enantiomerically p ure three (2S,3R) beta-hydroxy-alpha-amino acids (3) in excellent yiel d, (C) 1998 Elsevier Science Ltd. All rights reserved.