Highly Enantioselective Monofluoromethylation of C2-Arylindoles Using FBSM under Chiral Phase-Transfer Catalysis

被引：49

作者：

Matsuzaki, Kohei ^{[1
]}

Furukawa, Tatsuya ^{[1
]}

Tokunaga, Etsuko ^{[1
]}

Matsumoto, Takashi ^{[2
]}

Shiro, Motoo ^{[2
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

[2] Rigaku Corp, Akishima, Tokyo 1968666, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 13期

关键词：

BETA-SUBSTITUTED TRYPTOPHANS; MICHAEL ADDITION; NUCLEOPHILIC MONOFLUOROMETHYLATION; ALPHA; BETA-UNSATURATED ALDEHYDES; 3-(1-ARYLSULFONYLALKYL) INDOLES; ALLYLIC MONOFLUOROMETHYLATION; FLUORINATED SULFONES; ARYLSULFONYL INDOLES; FLUOROBIS(PHENYLSULFONYL)METHANE; DERIVATIVES;

D O I：

10.1021/ol4013102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3282 / 3285

页数：4

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