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

نویسندگان

  • Da-Wei Wang
  • Xiao-Bing Wang
  • Duo-Sheng Wang
  • Sheng-Mei Lu
  • Yong-Gui Zhou
  • Yu-Xue Li
چکیده

The enantioselective hydrogenation of 2-benzylquinolines and 2-functionalized and 2,3-disubstituted quinolines was developed by using the [Ir(COD)Cl](2)/bisphosphine/I(2) 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.

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منابع مشابه

Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines.

The highly enantioselective hydrogenation of quinoline derivatives is developed using [Ir(COD)Cl]2/(R)-MeO-Biphep/I2 system, and this methodology has been applied to the asymmetric synthesis of three naturally occurring alkaloids angustureine, galipinine, and cuspareine. This method provided an efficient access to a variety of optically active tetrahydroquinolines with up to 96% ee.

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عنوان ژورنال:
  • The Journal of organic chemistry

دوره 74 7  شماره 

صفحات  -

تاریخ انتشار 2009