Enantioselective Sulfur-Michael Addition of Thioacetic Acid to Nitroalkenes Catalyzed by Bifunctional Amine-Thiourea Catalysts

An enantioselective Michael addition of thioacetic acid (AcSH) to nitroalkenes, catalyzed by a leucine‐derived bifunctional aminethiourea, was developed with high yields and moderate enantioselectivities. The thiourea‐ammonium salt formed in the reaction is identified as the active catalyst, and th...

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Bibliographic Details
Published in:Helvetica chimica acta 2014-12, Vol.97 (12), p.1700-1707
Main Authors: Wang, Renchao, Xu, Jiaxi
Format: Article
Language:English
Subjects:
Alkenes
Alkenes, nitro
Aminethiourea catalyst
nitro
Sulfur-Michael addition
Thioacetic acid
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Summary:An enantioselective Michael addition of thioacetic acid (AcSH) to nitroalkenes, catalyzed by a leucine‐derived bifunctional aminethiourea, was developed with high yields and moderate enantioselectivities. The thiourea‐ammonium salt formed in the reaction is identified as the active catalyst, and the multiple H‐bonding system is responsible for the stereocontrol. The resulting thioester products are useful intermediates for the synthesis of enantiomerically enriched S‐containing compounds.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201400125