Enantioselective hydrogenation of β-ketoesters with monodentate ligands
Enantioselective hydrogenation of β-ketoesters with monodentate ligands
复制标题
DOI：
10.1002/anie.200460190
复制
发表时间：
2004-01-01
影响因子：
16.6
通讯作者：
Beller, M
中科院分区：
文献类型：
--
作者：
Junge, K;Hagemann, B;Beller, M
过渡金属催化的不对称反应为合成对映体纯的化合物提供了一种有效而优雅的可能性。[1]在各种催化方法中，对映选择性氢化反应在过去的二十年中得到了广泛的应用，并可能提供最重要的药物中间体。[2]在这方面，β-酮酯的氢化产生手性β-羟基酯，其是用于合成生物活性化合物和天然产物的有用结构单元（方案1）。[3] Noyori及其同事的开创性工作确立了使用binap作为这种转化的高度选择性配体。[4]手性配体的最新发展由Genet，[5] Weissensteiner和Spindler，[6] Imamoto，[7] Knochel，[8] Zhang，[9]等人的小组报道。[10]几乎所有已知的在β-酮酯的氢化中诱导显著的对映选择性的配体都是光学活性的二膦。[第十一届]
Transition-metal-catalyzed asymmetric reactions offer an efficient and elegant possibility for the synthesis of enantiomerically pure compounds.[1] Among the different catalytic methods, enantioselective hydrogenations have been used extensively in the last two decades and are likely to provide the most important access to pharmaceutical intermediates.[2] In this regard, the hydrogenation of β-ketoesters yields chiral β-hydroxyesters, which are useful building blocks for the synthesis of biologically active compounds and natural products (Scheme 1).[3]Pioneering work by Noyori and co-workers established the use of binap as a highly selective ligand for this transformation.[4] More recent developments of chiral ligands were reported by the groups of Genet,[5] Weissensteiner and Spindler,[6] Imamoto,[7] Knochel,[8] Zhang,[9] and others.[10] Virtually all known ligands that induce significant enantioselectivity in the hydrogenation of β-ketoesters are optically active diphosphines.[11]