Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines.
نویسندگان
چکیده
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.
منابع مشابه
A Highly Enantioselective Brønsted Acid Catalyzed Cascade Reaction: Organocatalytic Transfer Hydrogenation of Quinolines and their Application in the Synthesis of AlkaloidsThe authors acknowledge Degussa AG for generous funding
The enantioselective hydrogenation of olefins, ketones, and imines still represents an important topic in organic synthesis and catalysis. Although many highly enantioselective processes based on chiral Rh, Ru, and Ir complexes have been reported, most of these catalysts failed to give satisfactory results in the asymmetric hydrogenation of aromatic and heteroaromatic compounds. Examples of eff...
متن کاملHighly enantioselective iridium-catalyzed hydrogenation of 2-benzylquinolines and 2-functionalized and 2,3-disubstituted quinolines.
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(I...
متن کاملAsymmetric Hydrogenation of Quinolines and Isoquinolines Activated by ChloroformatesWe are grateful for the financial support from the National Science Foundation of China and Dalian Institute of Chemical Physics (K2004Eo3), Chinese Academy of Sciences
Despite significant progress in the area of asymmetric hydrogenation, the enantioselective hydrogenation of aromatic and heteroaromatic compounds still remains a major challenge. Only a few examples with moderate enantioselectivity, which rely on unique catalyst systems and suffer from a limited scope of suitable substrates, have been described so far. There are several reasons that might expla...
متن کاملAir-stable and phosphine-free iridium catalysts for highly enantioselective hydrogenation of quinoline derivatives.
Enantioselective hydrogenation of quinoline derivatives catalyzed by phosphine-free chiral cationic Cp*Ir(OTf)(CF 3TsDPEN) complex (CF 3TsDPEN = N-(p-trifluoromethylbenzenesulfonyl)-1,2-diphenylethylene-diamine) afforded the 1,2,3,4-tetrahydroquinoline derivatives in up to 99% ee. The reaction could be carried out with a substrate-to-catalyst molar ratio as high as 1000 in undegassed methanol a...
متن کاملAdvances in transition metal-catalyzed asymmetric hydrogenation of heteroaromatic compounds.
Transition metal-catalyzed asymmetric hydrogenation of heteroaromatic compounds is undoubtedly a straightforward and environmentally friendly method for the synthesis of a wide range of optically active heterocyclic compounds, which are widespread and ubiquitous in naturally occurring and artificial bioactive molecules. Over the past decade, a number of transition metal (Ir, Rh, Ru, and Pd) cat...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Journal of the American Chemical Society
دوره 125 35 شماره
صفحات -
تاریخ انتشار 2003