Communication
anti-Selective Asymmetric Michael Reactions of Aldehydes and Nitroolefins Catalyzed by a Primary Amine/Thiourea†
Hisatoshi Uehara Dr.,
Carlos F. Barbas III Prof. Dr.,
Hisatoshi Uehara Dr.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1) 858-784-2583 http://www.scripps.edu/mb/barbas
Search for more papers by this authorCarlos F. Barbas III Prof. Dr.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1) 858-784-2583 http://www.scripps.edu/mb/barbas
Search for more papers by this authorHisatoshi Uehara Dr.,
Carlos F. Barbas III Prof. Dr.,
Hisatoshi Uehara Dr.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1) 858-784-2583 http://www.scripps.edu/mb/barbas
Search for more papers by this authorCarlos F. Barbas III Prof. Dr.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1) 858-784-2583 http://www.scripps.edu/mb/barbas
Search for more papers by this author†
We thank the Skaggs Institute for Chemical Biology for funding.
Graphical Abstract
It′s finally here: Highly anti-selective Michael reactions of a functionalized aldehyde with nitroolefins have been realized using a primary amine/thiourea catalyst (see scheme; TBS=tert-butyldimethylsilyl). The reaction relies on a conformational strategy based on directing the formation of a Z-configured enamine intermediate.
Supporting Information
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- 14
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