INTRAMOLECULAR RING-CLEAVAGE OF CHIRAL TERPENOID-DERIVED OXAZINONE VIA ASYMMETRIC ANTI-ALDOL REACTION - UNEXPECTED ENTRY TO A N-SUBSTITUTEDTETRAHYDRO-1,3-OXAZINE-2,4-DIONE DERIVATIVE

Authors
ABBAS TR CADOGAN JIG DOYLE AA GOSNEY I HODGSON PKG HOWELLS GE HULME AN PARSONS S SADLER IH
Citation
Tr. Abbas et al., INTRAMOLECULAR RING-CLEAVAGE OF CHIRAL TERPENOID-DERIVED OXAZINONE VIA ASYMMETRIC ANTI-ALDOL REACTION - UNEXPECTED ENTRY TO A N-SUBSTITUTEDTETRAHYDRO-1,3-OXAZINE-2,4-DIONE DERIVATIVE, Tetrahedron letters, 38(27), 1997, pp. 4917-4920
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
27
Year of publication
1997
Pages
4917 - 4920
Database
ISI
SICI code
0040-4039(1997)38:27<4917:IROCTO>2.0.ZU;2-A
Abstract
In the presence of excess Bu2BOTf to promote anti-selectivity, an asym metric aldol reaction with a homochiral terpenoid-derived 1,3-oxazin-2 -one as the chiral control element results unexpectedly in ring cleava ge by an intramolecular process to form a N-substituted tetrahydro-1,3 -oxazine-2,4-dione in virtually quantitative yield. (C) 1997 Elsevier Science Ltd.