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双(烯基)硼酸酯的对映选择性联合交叉偶联:手性烯丙基硼试剂的通用合成方法

Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

作者信息

Edelstein Emma K, Namirembe Sheila, Morken James P

机构信息

Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.

出版信息

J Am Chem Soc. 2017 Apr 12;139(14):5027-5030. doi: 10.1021/jacs.7b01774. Epub 2017 Mar 29.

Abstract

Palladium-catalyzed conjunctive cross-coupling is used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsymmetric bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during the course of a Pd-induced metalate rearrangement.

摘要

钯催化的联合交叉偶联反应用于合成对映体富集的烯丙基硼试剂。该反应使用不对称双(烯基)硼酸酯作为底物,其反应机制似乎涉及选择性活化取代较少的烯烃,随后在钯诱导的金属盐重排过程中发生取代较多的烯烃迁移。

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