Asymmetric Hydrogenation of Heteroaromatic Ketones and Cyclic and Acyclic Enones Mediated by Cu(I)-Chiral Diphosphine Catalysts
Asymmetric Hydrogenation of Heteroaromatic Ketones and Cyclic and Acyclic Enones Mediated by Cu(I)-Chiral Diphosphine Catalysts
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DOI：
10.1055/s-0029-1218347
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发表时间：
2009-12-01
期刊：
影响因子：
2
通讯作者：
Mashima, Kazushi
中科院分区：
文献类型：
--
作者：
Shimizu, Hideo;Nagano, Takuto;Mashima, Kazushi
报道了铜催化的杂芳酮、环状和非环状烯酮的不对称氢化反应。手性双膦配体的选择高度影响对映选择性以及化学选择性。以BDPP为配体，实现了邻位取代杂芳酮的高对映选择性氢化。在丙烯烯酮的1，2-选择性加氢反应中，SEGPHOS的对映选择性高于BDPP.另一方面，大体积配体DTBM-SEGPHOS具有1，4-选择性的性质，导致第一个高1，4-选择性和对映选择性氢化环烯酮。
Copper(I)-catalyzed asymmetric hydrogenation of heteroaromatic ketones, cyclic and acyclic enones is reported. The choice of the chiral diphosphine ligand highly influenced enantioselectivity as well as chemoselectivity. Highly enantioselective hydrogenation Of ortho-substituted heteroaromatic ketones was achieved using BDPP as the ligand. In the 1,2-selective hydrogenation of acylic enone, SEGPHOS gave higher enantioselectivity than BDPP. On the other hand, the bulky ligand DTBM-SEGPHOS had a 1,4-selective nature, leading to the first highly 1,4-selective and enantioselective hydrogenation of cyclic enones.