Mechanistic and stereochemical aspects of the Lewis acid mediated cleavageof alpha-aminoacetals

Authors
Graham, MA Wadsworth, AH Thornton-Pett, M Carrozzini, B Cascarano, GL Rayner, CM
Citation
Ma. Graham et al., Mechanistic and stereochemical aspects of the Lewis acid mediated cleavageof alpha-aminoacetals, TETRAHEDR L, 42(15), 2001, pp. 2865-2868
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
15
Year of publication
2001
Pages
2865 - 2868
Database
ISI
SICI code
0040-4039(20010409)42:15<2865:MASAOT>2.0.ZU;2-U
Abstract
The TMSOTf mediated nucleophilic cleavage of alpha -aminoacetals can be use d to prepare a variety of substituted amines, with variable levels of stere ocontrol depending on the substitution patterns. The reaction most likely p roceeds via either an alpha -alkoxy aziridinium ion or an alpha -oxocarbeni um ion depending on the type of nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.