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Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.

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.

SUBMITTER: Nagib DA

PROVIDER: S-EPMC3310169 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.

Nagib David A DA Scott Mark E ME MacMillan David W C DW

Journal of the American Chemical Society 20090801 31

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 f ...[more]

PMID: 19722670

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