A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide

Authors
Barrow, JC Ngo, PL Pellicore, JM Selnick, HG Nantermet, PG
Citation
Jc. Barrow et al., A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide, TETRAHEDR L, 42(11), 2001, pp. 2051-2054
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
11
Year of publication
2001
Pages
2051 - 2054
Database
ISI
SICI code
0040-4039(20010311)42:11<2051:AFTSO1>2.0.ZU;2-Z
Abstract
Addition of organometallic reagents to tert-butylsulfinimines derived from tert-butyldimethylsiloxyacetaldehyde stereoselectively generates protected 1,2-amino alcohols. Removal of the acid labile protecting groups affords am ino alcohols in high yield. The predominant diastereomer is opposite to tha t predicted by the traditional Ellman model; therefore, a chelation model i nvoking rapid E/Z isomerization of the imine is proposed to rationalize the observed selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.