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Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis

Open access
Shih, Hui-Wen, Vander Wal, Mark N., Grange, Rebecca L., MacMillan, David W. C.·2010·Journal of the American Chemical Society

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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Authors
Shih, H.-W., Vander Wal, M. N., Grange, R. L., & MacMillan, D. W. C.
Venue
Journal of the American Chemical Society
Published
2010-09-10
Volume
132
Issue
39
Pages
13600-13603
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
OpenAlex
W1996259344
Cited by
509
References
0
FWCI
27.31
Type
journal article
Language
en
Open access
green

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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.