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

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

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 amino alcohols in high yield. The predominant diastereomer is opposite to tha...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters Vol. 42; no. 11; pp. 2051 - 2054
Main Authors: Barrow, James C, Ngo, Phung L, Pellicore, Janetta M, Selnick, Harold G, Nantermet, Philippe G
Format: Journal Article
Language:English
Published: Elsevier Ltd 11-03-2001
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 amino alcohols in high yield. The predominant diastereomer is opposite to that predicted by the traditional Ellman model; therefore, a chelation model invoking rapid E/ Z isomerization of the imine is proposed to rationalize the observed selectivity. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)00122-8