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. 2009 Aug 12;131(31):10875-7.
doi: 10.1021/ja9053338.

Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis

David A Nagib  1 , Mark E Scott, David W C MacMillan
Affiliations

Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis

David A Nagib et al. J Am Chem Soc. .

Abstract

The first enantioselective, organocatalytic alpha-trifluoromethylation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

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Figures

Scheme 1
Scheme 1
Proposed Merger of Catalytic Cycles for CF3-alkylation.
Scheme 2
Scheme 2
Access to Enantioenriched Organofluorine Synthons.
See this image and copyright information in PMC

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