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

被引：75

作者：

Barrow, JC ^{[1
]}

Ngo, PL ^{[1
]}

Pellicore, JM ^{[1
]}

Selnick, HG ^{[1
]}

Nantermet, PG ^{[1
]}

机构：

[1] Merck Res Labs, W Point, PA 19486 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(01)00122-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2051 / 2054

页数：4

共 19 条

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