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. 2010 Oct 6;132(39):13600-3.
doi: 10.1021/ja106593m.

Enantioselective α-benzylation of aldehydes via photoredox organocatalysis

Hui-Wen Shih  1 , Mark N Vander Wal, Rebecca L Grange, David W C MacMillan
Affiliations

Enantioselective α-benzylation of aldehydes via photoredox organocatalysis

Hui-Wen Shih et al. J Am Chem Soc. .

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.

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Figures

Figure 1
Figure 1
Proposed catalytic cycle for aldehyde α-benzylation.
Figure 2
Figure 2
Fluorescence quenching by reaction substrates.
See this image and copyright information in PMC

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