期刊
ORGANIC LETTERS
卷 24, 期 25, 页码 4699-4703出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01972
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资金
- JSPS KAKENHI [JP20H00380, JP20H04826, JP20K15287]
In this study, an enantioselective Friedel-Crafts alkylation reaction was developed using chiral phosphoric acid as the catalyst to react N-unprotected alkynyl trifluoromethyl ketimines with pyrroles, resulting in the synthesis of chiral primary alpha-trifluoromethyl-alpha-(2-pyrrolyl)propargyl-amines with high enantioselectivity. The alkynyl group of the adducts can be transformed without a loss of optical purity, leading to optically active alpha-trifluoromethylated amines bearing various substituents.
Developed herein is an enantioselective Friedel-Crafts alkylation reaction of N-unprotected alkynyl trifluoromethyl ketimines with pyrroles catalyzed by chiral phosphoric acid to furnish chiral primary alpha-trifluoromethyl-alpha-(2-pyrrolyl)propargyl-amines with high enantioselectivity. Transformation of the alkynyl group of the adducts afforded optically active alpha-trifluoromethylated amines bearing various substituents such as alkyl, alkenyl, enyne, and triazole without loss of optical purity.
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