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铜催化烯胺的不对称1,2-芳基硼化反应:合成含手性硼酸酯的3,3'-二取代异吲哚啉酮

Copper-catalyzed asymmetric 1,2-arylboration of enamines: access to chiral borate-containing 3,3'-disubstituted isoindolinones.

作者信息

Xie Jia-Qi, Wang Bing-Xia, Liang Ren-Xiao, Jia Yi-Xia

机构信息

College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, China.

School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China.

出版信息

Org Biomol Chem. 2024 Jul 31;22(30):6085-6089. doi: 10.1039/d4ob00896k.

Abstract

An enantioselective copper-catalyzed 1,2-arylboration reaction of enamines has been developed by employing ()-xyl-BINAP as a chiral ligand. A number of chiral borate-containing 3,3'-disubstituted isoindolinones were obtained in moderate to good yields and good to excellent enantioselectivities from the reactions of -(-iodobenzoyl)enamines and bis(pinacolato)diboron (Bpin) under mild reaction conditions. Synthetic transformations of the products were conducted to demonstrate the practicality of this reaction.

摘要

通过使用()-木糖-BINAP作为手性配体,开发了一种对映选择性铜催化的烯胺1,2-芳基硼化反应。在温和的反应条件下,通过-(-碘苯甲酰基)烯胺与双(频哪醇合)二硼(Bpin)的反应,以中等至良好的产率和良好至优异的对映选择性获得了许多含手性硼酸酯的3,3'-二取代异吲哚啉酮。对产物进行了合成转化,以证明该反应的实用性。

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