187523-35-9Relevant articles and documents
Enantioselective fluorination mediated by N-fluoroammonium salts of cinchona alkaloids: First enantioselective synthesis of BMS-204352 (maxipost)
Shibata, Norio,Ishimaru, Takehisa,Suzuki, Emiko,Kirk, Kenneth L.
, p. 2494 - 2497 (2003)
We have employed a cinchona alkaloid/Select-fluor-mediated enantioselective fluorination of the oxindole 2 to achieve the first enantioslective synthesis of BMS-204352 (MaxiPost, S-1), an effective opener of maxi-K channels. Fluorination occurred to produce S-1 with 84% ee using the bis-cinchona alkaloid (DHQ)2AQN. Recrystallization produced enantiomerically pure (>99% ee) product. Quinidine-mediated fluorination of 2 gave the (R)-antipode of 1 with 68% ee.
Highly enantioselective fluorination of unprotected 3-substituted oxindoles: One-step synthesis of BMS 204352 (MaxiPost)
Li, Jun,Cai, Yunfei,Chen, Weiliang,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
, p. 9148 - 9155,8 (2012/12/12)
The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N′-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.
Catalytic enantioselective fluorination of oxindoles
Hamashima, Yoshitaka,Suzuki, Toshiaki,Takano, Hisashi,Shimura, Yuta,Sodeoka, Mikiko
, p. 10164 - 10165 (2007/10/03)
We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluor
