Asymmetric Synthesis of Chiral Spiroketal Bisphosphine Ligands and Their Application in Enantioselective Olefin Hydrogenation.
Asymmetric Synthesis of Chiral Spiroketal Bisphosphine Ligands and Their Application in Enantioselective Olefin Hydrogenation.
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DOI：
10.1021/acs.joc.8b01693
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发表时间：
2018-09
期刊：
影响因子：
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通讯作者：
Jian Huang;Mao-Chun Hong;Chuan‐Chuan Wang;S. Kramer;G. Lin;Xingwen Sun
中科院分区：
文献类型：
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作者：
Jian Huang;Mao-Chun Hong;Chuan‐Chuan Wang;S. Kramer;G. Lin;Xingwen Sun
通过不对称合成得到了一系列含1，1 '-螺环（3 H，3' H）异苯并呋喃骨架的手性螺缩酮双膦配体，并在铑催化的α-脱氢氨基酸酯的不对称选择性氢化反应中进行了研究.配体提供了最高的对映选择性（高达99.5%），在七个步骤中获得的总收率为38%。该合成可以在克级规模上进行，并且不需要对映体的动力学拆分。总的来说，所开发的配体提供了SDP配体以及其他手性双膦配体的容易获得的替代品。
A series of chiral spiroketal bisphosphine ligands containing 1,1'-spirobi(3 H,3' H)isobenzofuran backbones was accessed through asymmetric synthesis and subsequently tested in enantioselective Rh-catalyzed hydrogenation of α-dehydroamino acid esters. The ligand providing the highest enantioselectivity (up to 99.5%) was obtained in seven steps in an overall 38% yield. The synthesis could be performed on a gram scale, and no kinetic resolution of enantiomers is required. Overall, the developed ligand provides an easily accessible alternative to SDP ligands as well as other chiral bisphosphine ligands.