Regio- and stereoselective ring contraction of 1,2-dithianes to 1,2-dithiolanes

被引：0
|
作者：
Mansour, Tarek S. [1 ]
Evans, Colleen A. [2 ]
Bogucki, David E. [3 ]
Chowdhury, Sultan [3 ]
机构：
[1] Sabila Biosci LLC, 5 Overlook Rd, New City, NY 10956 USA
[2] Dominican Univ New York, Sci Dept, 470 Western Highway, Orangeburg, NY 10962 USA
[3] Syrachem Sci Inc, 7007-180 St, Surrey, BC V3S 7S3, Canada
来源：
TETRAHEDRON LETTERS | 2023年 / 121卷
关键词：
Ring-contraction; 12; dithianes; 1; 2-dithiolanes; S-episulfonium;
D O I：
10.1016/j.tetlet.2023.154485
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Monobenzoylated 1,2-dithiane-4,5 diols undergo a novel ring contraction reaction under Mitsunobu con-ditions to produce 3,4-disubstituted 1,2-dithiolanes. This transformation is stereoselective and proceeds with retention of configuration. The yields for the trans isomers are higher than those of the cis series for a variety of O, N and S nucleophiles. A plausible pathway for forming the 1,2-dithiolanes involves the for-mation of a S-episulfonium intermediates.(c) 2023 Elsevier Ltd. All rights reserved.
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页数：5
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