The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3‐Aliphatic‐Substituted Indoles and Pyrroles | Zendy

Huestis Malcolm P. | Zendy; Chan Lina | Zendy; Stuart David R. | Zendy; Fagnou Keith | Zendy

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The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3‐Aliphatic‐Substituted Indoles and Pyrroles

Author(s) -

Huestis Malcolm P.,

Chan Lina,

Stuart David R.,

Fagnou Keith

Publication year - 2011

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201006381

Subject(s) - regioselectivity , moiety , pyrrole , indole test , yield (engineering) , chemistry , organic chemistry , aryl , catalysis , combinatorial chemistry , materials science , alkyl , metallurgy

Rho‐Rho‐Rho your boat : A rhodium catalyst effects the regioselective oxidative coupling of enynes with N ‐aryl ureas (X=NR 2 ) and N ‐vinylacetamides (X=C(O)Me), affording the corresponding 2‐alkenylindoles and 2‐alkenylpyrroles in good yield. Simple hydrogenation delivers the C2/C3‐aliphatic‐substituted indole or pyrrole (see scheme).

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