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Enantioselective Intramolecular Aldehyde α-Alkylation with Simple Olefins: Direct Access to Homo-Ene Products

Author:
Comito, Robert J., Finelli, Fernanda G., MacMillan, David W. C.
Source:
Journal of the American Chemical Society 2013 v.135 no.25 pp. 9358-9361
ISSN:
1520-5126
Subject:
aldehydes, alkenes, cations, enantiomers
Abstract:
A highly selective method for the synthesis of asymmetrically substituted carbocycles and heterocycles from unactivated aldehyde–olefin precursors has been achieved via enantioselective SOMO-catalysis. Addition of a catalytically generated enamine radical cation across a pendent olefin serves to establish a general asymmetric strategy toward the production of a wide range of formyl-substituted rings with alkene transposition. Conceptually, this novel mechanism allows direct access to “homo-ene”-type products.
Agid:
5388769