Iridium-catalyzed asymmetric hydrogenation of dibenzo[<em>b,f</em>][1,4]thiazepines

Guo, Ran-Ning; Gao, Kai; Ye, Zhi-Shi; Shi, Lei; Li, Yanqin; Zhou, Yong-Gui

doi:10.1351/PAC-CON-12-07-02

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Pure Appl. Chem., 2013, Vol. 85, No. 4, pp. 843-849

http://dx.doi.org/10.1351/PAC-CON-12-07-02

Published online 2013-01-26

Iridium-catalyzed asymmetric hydrogenation of dibenzo[b,f][1,4]thiazepines

Ran-Ning Guo^1,2, Kai Gao², Zhi-Shi Ye², Lei Shi², Yanqin Li¹ and Yong-Gui Zhou²*

¹ Department of Chemistry, Dalian University of Technology, Dalian 116012, China
² State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China

Abstract: Highly enantioselective hydrogenation of substituted dibenzo[b,f][1,4]thiazepines was achieved with up to 96 % ee (enantiomeric excess) using [Ir(COD)Cl]₂/(R)-SynPhos complex as catalyst in the presence of iodine. This method provides an efficient access to optically active 11-substituted-10,11-dihydrodibenzo[b,f][1,4]thiazepines.