A highly stereo-divergent Mannich-type reaction catalyzed by Bronsted acidin aqueous media

Authors
Akiyama, T Takaya, J Kagoshima, H
Citation
T. Akiyama et al., A highly stereo-divergent Mannich-type reaction catalyzed by Bronsted acidin aqueous media, TETRAHEDR L, 42(24), 2001, pp. 4025-4028
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
24
Year of publication
2001
Pages
4025 - 4028
Database
ISI
SICI code
0040-4039(20010611)42:24<4025:AHSMRC>2.0.ZU;2-T
Abstract
anti And syn stereoselectivity on the HBF4-catalyzed Mannich-type reaction of ketene silyl acetal derived from cc-oxy esters with aldimines were inves tigated. Whereas use of ketene silyl acetal derived from aryl ester in aque ous 2-propanol gave anti beta -amino-alpha -siloxy ester with excellent ste reoselectivity, use of ketene silyl acetal derived from methyl ester in wat er in the presence of sodium dodecyl sulfate gave the syn isomer preferenti ally. (C) 2001 Elsevier Science Ltd. All rights reserved.