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
收藏
页码：6438 / 6446
页数：9
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