Highly enantioselective monofluoromethylation of C2-arylindoles using FBSM under chiral phase-transfer catalysis

Kohei Matsuzaki; Tatsuya Furukawa; Etsuko Tokunaga; Takashi Matsumoto; Motoo Shiro; Norio Shibata

doi:10.1021/ol4013102

Highly enantioselective monofluoromethylation of C2-arylindoles using FBSM under chiral phase-transfer catalysis

Org Lett. 2013 Jul 5;15(13):3282-5. doi: 10.1021/ol4013102. Epub 2013 Jun 17.

Authors

Kohei Matsuzaki¹, Tatsuya Furukawa, Etsuko Tokunaga, Takashi Matsumoto, Motoo Shiro, Norio Shibata

Affiliation

¹ Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.

PMID: 23773074
DOI: 10.1021/ol4013102

Abstract

The highly enantioselective addition of 1-fluoro-1,1-bis(phenylsulfonyl)methane (FBSM) to vinylogous imines generated in situ from 2-aryl-3-(1-arylsulfonylmethyl)indoles was achieved using chiral ammonium salts derived from cinchona alkaloids. One-pot conversion from 2-arylindoles with FBSM was also adaptable under the same reaction conditions. The key for this transformation is the effective use of the arylsulfonyl group.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ammonium Compounds / chemistry*
Catalysis
Cinchona Alkaloids / chemistry*
Indoles / chemistry*
Methylation
Molecular Structure
Phase Transition
Stereoisomerism
Sulfhydryl Compounds / chemistry*

Substances

1-fluoro-1,1-bis(phenylsulfonyl)methane
Ammonium Compounds
Cinchona Alkaloids
Indoles
Sulfhydryl Compounds