STUDIES INTO THE ASYMMETRIC MEISENHEIMER REARRANGEMENT

Authors
BUSTON JEH COLDHAM I MULHOLLAND KR
Citation
Jeh. Buston et al., STUDIES INTO THE ASYMMETRIC MEISENHEIMER REARRANGEMENT, Tetrahedron : asymmetry, 9(11), 1998, pp. 1995-2009
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
11
Year of publication
1998
Pages
1995 - 2009
Database
ISI
SICI code
0957-4166(1998)9:11<1995:SITAMR>2.0.ZU;2-P
Abstract
Oxidation of a variety of N-allyl prolinol derivatives gave amine N-ox ides with complete diastereoselectivity. On warming, these amine N-oxi des undergo [2,3]-Meisenheimer rearrangement to give O-allyl hydroxyla mines, albeit with low diastereoselectivity. Attempts to promote asymm etric N-oxidation of N-allyl tertiary amines with a variety of asymmet ric oxidants produced only racemic N-oxides. (C) 1998 Elsevier Science Ltd. All rights reserved.