A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF TRICYCLIC LACTAMS AND THEIR APPLICATION AS NOVEL N-ACYL IMINIUM ION PRECURSORS IN THE SYNTHESIS OFISOINDOLINONE DERIVATIVES

Authors
ALLIN SM NORTHFIELD CJ PAGE MI SLAWIN AMZ
Citation
Sm. Allin et al., A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF TRICYCLIC LACTAMS AND THEIR APPLICATION AS NOVEL N-ACYL IMINIUM ION PRECURSORS IN THE SYNTHESIS OFISOINDOLINONE DERIVATIVES, Tetrahedron letters, 38(20), 1997, pp. 3627-3630
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
20
Year of publication
1997
Pages
3627 - 3630
Database
ISI
SICI code
0040-4039(1997)38:20<3627:AHDSOT>2.0.ZU;2-P
Abstract
Condensation of 2-formylbenzoic acid with alpha-amino alcohol substrat es proceeds with extremely high diastereoselectivity to produce tricyc lic gamma-lactam products. The relative stereochemistry of the major d iastereoisomer has been determined by X-ray crystal analysis and a mec hanism suggested to explain the stereochemical outcome. Further, we re port that this class of heterocycle can act as an N-acyl iminium ion p recursor in the synthesis of substituted isoindolinone derivatives. (C ) 1997 Elsevier Science Ltd.