Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis

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 di...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2010-10, Vol.132 (39), p.13600-13603
Main Authors: Shih, Hui-Wen, Vander Wal, Mark N., Grange, Rebecca L., MacMillan, David W. C.
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Catalysis
Crystallography, X-Ray
Imidazolidines - chemistry
Iridium - chemistry
Models, Molecular
Molecular Structure
Oxidation-Reduction
Photochemistry
Stereoisomerism
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja106593m