Catalytic Thia-Sommelet−Hauser Rearrangement: Application to the Synthesis of Oxindoles

A series of 3-arylthio-1,3-disubstituted-oxindoles were prepared in good yields by the reaction of α-diazocarbonyl compounds and sulfenamides. The reaction involves a Rh-catalyzed thia-Sommelet−Hauser-type rearrangement.

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Bibliographic Details
Published in:Organic letters 2011-03, Vol.13 (5), p.1210-1213
Main Authors: Li, Yuye, Shi, Yi, Huang, Zhongxing, Wu, Xinhu, Xu, Pengfei, Wang, Jianbo, Zhang, Yan
Format: Article
Language:English
Subjects:
Azo Compounds - chemistry
Catalysis
Crystallography, X-Ray
Indoles - chemical synthesis
Indoles - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Rhodium - chemistry
Stereoisomerism
Sulfonamides - chemistry
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Summary:A series of 3-arylthio-1,3-disubstituted-oxindoles were prepared in good yields by the reaction of α-diazocarbonyl compounds and sulfenamides. The reaction involves a Rh-catalyzed thia-Sommelet−Hauser-type rearrangement.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200091k