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N,N-DIALKYLTHIOAMIDES IN THE MICHAEL ADDITION TO CONJUGATE CARBONYL COMPOUNDS, REGIOSELECTIVITY, STEREOCHEMISTRY AND MECHANISM

 

作者: Lilia Viteva,   Tzveta Gospodova,   Yuri Stefanovsky,  

 

期刊: Phosphorus, Sulfur, and Silicon and the Related Elements  （Taylor Available online 1993）
卷期: Volume 78, issue 1-4  

页码: 189-198

 

ISSN:1042-6507

 

年代: 1993

 

DOI:10.1080/10426509308032434

 

出版商: Taylor & Francis Group

 

关键词: N,N-dialkylthioamides;Michael reaction;regioselectivity;diastereoselectivity;transition state

 

数据来源: Taylor

 

摘要:

The regio- and diastereoselectivity of the addition ofN,N-dialkylphenylthioacetamide enolates to some conjugate carbonyl compounds are studied. The results are compared with oxoanalogs and the differences are rationalized in terms of specific behaviour of sulfur. General trend to 1,4-addition is demonstrated. The stereochemistry is correlated with the cyclic transition state taking into account the ground state conformation preferred by the acceptor.

 

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