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Synfacts 2014; 10(8): 0835
DOI: 10.1055/s-0034-1378423
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Lewis Acid/Brønsted Base Catalyzed Michael Addition to Thioamides

Contributor(s):
Hisashi Yamamoto
,
Yasushi Shimoda
Yin L, Takada H, Lin S, Kumagai N, * Shibasaki M. * Institute of Microbial Chemistry (BIKAKEN), Tokyo, Japan
Direct Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated Butyrolactones to α,β-Unsaturated Thioamides.

Angew. Chem. Int. Ed. 2014;
53: 5327-5331
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Further Information

Publication History

Publication Date:
18 July 2014 (online)

 
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Key words

copper - Michael addition - thioamides

Significance

The authors developed a highly stereoselective conjugate addition of butyrolactones to unsaturated thioamides. The combination of soft Lewis acid and Brønsted base enabled this transformation with excellent atom economy.


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Comment

Noteworthy, this reaction could be conducted in more than one gram scale under mild conditions. The obtained thioamides are transformed into various functional groups in one step.


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