NADH MODELS IN THE PYRROLO[3,4-B]PYRIDINE SERIES - ROLE OF THE CYCLIZED STRUCTURE IN THE STEREOCONTROL OF REDUCTIONS

Authors
BEDAT J LEVACHER V DUPAS G QUEGUINER G BOURGUIGNON J
Citation
J. Bedat et al., NADH MODELS IN THE PYRROLO[3,4-B]PYRIDINE SERIES - ROLE OF THE CYCLIZED STRUCTURE IN THE STEREOCONTROL OF REDUCTIONS, Chemistry Letters, (4), 1995, pp. 327-328
Citations number
18
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
4
Year of publication
1995
Pages
327 - 328
Database
ISI
SICI code
0366-7022(1995):4<327:NMITPS>2.0.ZU;2-Z
Abstract
The synthesis of a chiral NADH model in pyrrolo[3,4-b] pyridine series is described and the asymmetric reduction of methyl benzoylformate is studied. Its asymmetric behavior compared with a cyclized analogue in naphthyridine series suggests that the orientation of the carbonyl gr oup of the lactam plays an important role in the stereochemical contro l of the reduction.