Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

被引:837
作者
Nagib, David A. [1 ]
Scott, Mark E. [1 ]
MacMillan, David W. C. [1 ]
机构
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
关键词
SILYL ENOL ETHERS; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; RADICAL TRIFLUOROMETHYLATION; MEDICINAL CHEMISTRY; CARBONYL-COMPOUNDS; ORGANIC-MOLECULES; CATALYSIS; PERFLUOROALKYLATION; FLUORINE; POTENTIALS;
D O I
10.1021/ja9053338
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first enantioselective, organocatalytic alpha-trifluoromethytation 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.
引用
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页码:10875 / +
页数:4
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