Work

Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis

Year: 2010

Type: article

Abstract: The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity. The utility of this methodology has been demonstrated via rapid access to an enantioenriched drug target for angiogenesis suppression.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja106593m

Authors: Hui-Wen Shih, Mark N. Vander Wal, Rebecca L. Grange, David W. C. MacMillan

Institution: Princeton University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: New Strategies in Metallaphotoredox Catalysis, G7747101108