Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas | Zendy

Isabelle Aillaud | Zendy; David M. Barber | Zendy; Amber L. Thompson | Zendy; Darren J. Dixon | Zendy

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Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas

Author(s) -

Isabelle Aillaud,

David M. Barber,

Amber L. Thompson,

Darren J. Dixon

Publication year - 2013

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol401039h

Subject(s) - iminium , tryptamine , chemistry , moiety , enantioselective synthesis , organocatalysis , phosphoric acid , urea , catalysis , organic chemistry , michael reaction , combinatorial chemistry , cascade , biochemistry , chromatography

A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities.

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