4.8 Article

Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 39, Pages 13600-13603

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja106593m

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Funding

  1. NIHGMS [R01 01 GM093213-01]

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The first enantioselective aldehyde alpha-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.

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