Application of amide-stabilized sulfur ylide reactivity to the stereodivergent synthesis of (R,S)- and (S,R)-reboxetine

被引：24

作者：

Aparicio, David M. ^{[1
]}

Teran, Joel L. ^{[1
]}

Gnecco, Dino ^{[1
]}

Galindo, Alberto ^{[1
]}

Juarez, Jorge R. ^{[1
]}

Orea, Maria L. ^{[1
]}

Mendoza, Angel ^{[1
]}

机构：

[1] Benemerita Univ Autonoma Puebla, Ctr Quim, Puebla 72570, Pue, Mexico

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 23期

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; GLYCIDIC AMIDES; DERIVATIVES; REBOXETINE; EPOXIDATION; (S; S)-REBOXETINE; ENANTIOMERS; MECHANISM; HYDROXY;

D O I：

10.1016/j.tetasy.2009.12.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple access to (RS)- and (S,R)-reboxetine from a single chiral sulfonium salt 4 is reported. This approach, based on a stabilized sulfur ylide-mediated epoxidation, followed by a regioselective opening reaction, enables the preparation of these two potentially biologically active compounds in 35.6% and 13.7% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2764 / 2768

页数：5

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