Highly enantioselective monofluoromethylation of C2-arylindoles using FBSM under chiral phase-transfer catalysis was written by Matsuzaki, Kohei;Furukawa, Tatsuya;Tokunaga, Etsuko;Matsumoto, Takashi;Shiro, Motoo;Shibata, Norio. And the article was included in Organic Letters in 2013.Reference of 69221-14-3 This article mentions the following:
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 e. g., I with FBSM was also adaptable under the same reaction conditions. The key for this transformation is the effective use of the arylsulfonyl group. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Reference of 69221-14-3).
(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.Reference of 69221-14-3
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider