Jump to Main Content
Enantioselective Intramolecular Aldehyde α-Alkylation with Simple Olefins: Direct Access to Homo-Ene Products
- Comito, Robert J., Finelli, Fernanda
G., MacMillan, David W. C.
- Journal of the American Chemical Society 2013 v.135 no.25 pp. 9358-9361
- aldehydes, alkenes, cations, enantiomers
- 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.