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
收藏
页码：3282 / 3285
页数：4
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