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Enantioselective Organocatalytic Singly Occupied Molecular Orbital Activation: The Enantioselective α-Enolation of Aldehydes

Hye-Young Jang, Jun-Bae Hong and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, Email: dmacmillprinceton.edu

H.-Y. Jang, J.-B. Hong, D. W. C. MacMillan, J. Am. Chem. Soc., 2007, 129, 7004-7005.

DOI: 10.1021/ja0719428 (free Supporting Information)


Abstract

Singly occupied molecular orbital (SOMO) catalysis allows an enantioselective organocatalytic α-enolation of aldehydes. A chiral secondary amine catalyst reacts with aldehydes to form transient enamines that undergo selective one-electron oxidation to generate SOMO-activated electrophilic radical cations which are susceptible to attack by ketone-derived enol silanes.

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Key Words

1,4-diketones, organocatalysis, CAN


ID: J48-Y2007-1780