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手性氢钯和烯胺催化协同实现醛与炔烃的不对称 α-烯丙基化反应。

Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis.

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry , University of Science and Technology of China , Hefei , 230026 , China.

Collaborative Innovation Center of Chemical Science and Engineering, Tianjin , China.

出版信息

Org Lett. 2018 Apr 20;20(8):2403-2406. doi: 10.1021/acs.orglett.8b00740. Epub 2018 Apr 5.

DOI:10.1021/acs.orglett.8b00740
PMID:29620907
Abstract

A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.

摘要

钯催化的醛与炔烃的不对称 α-烯丙基化反应通过整合烯胺和手性氢化钯络合物的催化作用得以实现,后者是由 Pd(0) 对手性磷酸的氧化加成可逆形成的。该三元催化剂体系由非手性钯配合物、伯胺和手性磷酸组成,允许反应容忍广泛的α,α-二取代醛和炔烃,以高收率和优异的对映选择性得到相应的烯丙基化产物。

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