PREPARATION OF ENANTIOMERICALLY PURE FRUCTOSE-DERIVED 1,3-OXAZIN-2-ONE BY INIR METHODOLOGY AND ITS APPLICATION AS A CHIRAL AUXILIARY IN SOME MODEL ASYMMETRIC REACTIONS

Authors
BANKS MR CADOGAN JIG GOSNEY I GOULD RO HODGSON PKG MCDOUGALL D
Citation
Mr. Banks et al., PREPARATION OF ENANTIOMERICALLY PURE FRUCTOSE-DERIVED 1,3-OXAZIN-2-ONE BY INIR METHODOLOGY AND ITS APPLICATION AS A CHIRAL AUXILIARY IN SOME MODEL ASYMMETRIC REACTIONS, Tetrahedron, 54(33), 1998, pp. 9765-9784
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
33
Year of publication
1998
Pages
9765 - 9784
Database
ISI
SICI code
0040-4020(1998)54:33<9765:POEPF1>2.0.ZU;2-L
Abstract
A newly developed fructose-based homochiral 1,3-oxazin-2-one reagent p repared via a regioselective and stereoselective intramolecular nitren e insertion reaction (INIR) exerts smooth stereocontrol resulting in h igh levels of asymmetric induction and chemical yield in various synth etic transformations including aldol, Diels-Alder cycloaddition and al pha-bromination reactions. (C) 1998 Elsevier Science Ltd. All rights r eserved.