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钯(II)催化芳基硼酸对丙二酸亚异丙酯衍生二烯的不对称1,6-共轭加成反应。

Pd(ii)-Catalyzed asymmetric 1,6-conjugate addition of arylboronic acids to Meldrum's acid-derived dienes.

作者信息

Chen Song, Wu Liang, Shao Qihang, Yang Guoqiang, Zhang Wanbin

机构信息

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.

出版信息

Chem Commun (Camb). 2018 Mar 6;54(20):2522-2525. doi: 10.1039/c8cc00493e.

DOI:10.1039/c8cc00493e
PMID:29461550
Abstract

A Pd(ii)-catalyzed asymmetric 1,6-addition of arylboronic acids to Meldrum's acid-derived dienes was developed. A new substituted In-Pyrox ligand was designed to enable this reaction with high enantioselectivity via a remote steric effect. A series of Meldrum's acid-derived dienes and arylboronic acids were tolerable to the reaction conditions, giving the desired adducts in moderate to high yields with good enantioselectivities (up to 96% ee). This reaction provides the first method of Pd(ii)-catalyzed asymmetric 1,6-conjugate addition of arylboron.

摘要

开发了一种钯(II)催化的芳基硼酸对丙二酸亚异丙酯衍生二烯的不对称1,6-加成反应。设计了一种新型取代的In-Pyrox配体,通过远程空间效应使该反应具有高对映选择性。一系列丙二酸亚异丙酯衍生的二烯和芳基硼酸对反应条件具有耐受性,以中等至高产率和良好的对映选择性(高达96% ee)得到所需的加合物。该反应提供了第一种钯(II)催化的芳基硼不对称1,6-共轭加成方法。

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