ASYMMETRIC HETERO-DIELS-ALDER REACTION OF N-BENZYLIMINES DERIVED FROMR-GLYCERALDEHYDE - A NEW APPROACH TO HOMOCHIRAL PIPERIDINE BUILDING-BLOCKS AND ITS APPLICATION TO THE SYNTHESIS OF (2R)-4-OXOPIPECOLIC ACID

Authors
BADORREY R CATIVIELA C DIAZDEVILLEGAS MD GALVEZ JA
Citation
R. Badorrey et al., ASYMMETRIC HETERO-DIELS-ALDER REACTION OF N-BENZYLIMINES DERIVED FROMR-GLYCERALDEHYDE - A NEW APPROACH TO HOMOCHIRAL PIPERIDINE BUILDING-BLOCKS AND ITS APPLICATION TO THE SYNTHESIS OF (2R)-4-OXOPIPECOLIC ACID, Tetrahedron letters, 38(14), 1997, pp. 2547-2550
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
14
Year of publication
1997
Pages
2547 - 2550
Database
ISI
SICI code
0040-4039(1997)38:14<2547:AHROND>2.0.ZU;2-M
Abstract
The N-Benzyl imine derived from 23-di-O-benzyl-D-glyceraldehyde reacts with Danishefsky's diene to afford the corresponding hetero Diels-Ald er adduct with a high diastereoselectivity. This compound can be trans formed to enantiomerically pure (2R)-4-oxopipecolic acid. (C) 1997 Els evier Science Ltd.