钯催化芳基硼酸对α,β-不饱和环状亲电试剂的不对称共轭加成反应
Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Cyclic Electrophiles.
作者信息
Shockley Samantha E, Holder Jeffrey C, Stoltz Brian M
机构信息
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
出版信息
Org Process Res Dev. 2015 Aug 21;19(8):974-981. doi: 10.1021/acs.oprd.5b00169. Epub 2015 Jul 2.
Abstract
This account describes our laboratory's efforts in the development of a palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic conjugate acceptors. Specifically, we highlight the study of this transformation in the following areas: (a) construction of all-carbon quaternary stereocenters, (b) elucidation of the reaction mechanism,
摘要
本报告描述了我们实验室在开发钯催化芳基硼酸与环状共轭受体的不对称共轭加成反应方面所做的工作。具体而言，我们重点介绍了该转化反应在以下几个方面的研究：(a) 全碳季碳立体中心的构建，(b) 反应机理的阐明。
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Organic Synth. 2016;92. doi: 10.1002/0471264229.os092.19. Epub 2016 Mar 4.
2
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3
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