Highly enantioselective iridium-catalyzed hydrogenation of 2-benzylquinolines and 2-functionalized and 2, 3-disubstituted quinolines

DW Wang, XB Wang, DS Wang, SM Lu…

Index: Wang, Da-Wei; Wang, Xiao-Bing; Wang, Duo-Sheng; Lu, Sheng-Mei; Zhou, Yong-Gui; Li, Yu-Xue Journal of Organic Chemistry, 2009 , vol. 74, # 7 p. 2780 - 2787

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Citation Number: 125

Abstract

The enantioselective hydrogenation of 2-benzylquinolines and 2-functionalized and 2, 3- disubstituted quinolines was developed by using the [Ir (COD) Cl] 2/bisphosphine/I2 system with up to 96% ee. Moreover, mechanistic studies revealed the hydrogenation mechanism of quinoline involves a 1, 4-hydride addition, isomerization, and 1, 2-hydride addition, and the catalytic active species may be a Ir (III) complex with chloride and iodide.

~32%

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