TBD-catalyzed α-sulfenylation of cyclic ketones: desymmetrization of 4-substituted cyclohexanones

被引：10

作者：

Poladura, Belen ^{[1
]}

Martinez-Castaneda, Angel ^{[1
]}

Rodriguez-Solla, Humberto ^{[1
]}

Concellon, Carmen ^{[1
]}

del Amo, Vicente ^{[1
]}

机构：

[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain

来源：

TETRAHEDRON | 2012年 / 68卷 / 32期

关键词：

Organocatalysis; Guanidines; Stereoselective reactions; DIRECT ALDOL REACTION; GUANIDINES; EPOXIDES; THIOLS;

D O I：

10.1016/j.tet.2012.05.124

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A low loading of triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzes the alpha-sulfenylation reaction of ketones employing tetramethylthiuram disulfide (TMTDS) as electrophilic reagent. This methodology is mild, effective and straightforward, rendering the desired products in high yield. Prochiral 4-substituted cyclohexanones can be desymmetrized with remarkable diastereoselectivity following this protocol. The dithiocarbamoyl function was shown to be easily removed upon reduction, affording thiols (1-mercaptan-2-ols). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6438 / 6446

页数：9

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