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Enantioselective intramolecular aldehyde ?-alkylation with simple olefins: direct access to homo-ene products.

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.

SUBMITTER: Comito RJ 

PROVIDER: S-EPMC3746539 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Enantioselective intramolecular aldehyde α-alkylation with simple olefins: direct access to homo-ene products.

Comito Robert J RJ   Finelli Fernanda G FG   MacMillan David W C DW  

Journal of the American Chemical Society 20130612 25

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"-  ...[more]

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