Direct Access to Chiral Secondary Amides by Copper-Catalyzed Borylative Carboxamidation of Vinylarenes with Isocyanates
Direct Access to Chiral Secondary Amides by Copper-Catalyzed Borylative Carboxamidation of Vinylarenes with Isocyanates
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DOI：
10.1021/jacs.9b12297
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发表时间：
2020-01-08
影响因子：
15
通讯作者：
Mazet, Clement
中科院分区：
文献类型：
--
作者：
Fiorito, Daniele;Liu, Yangbin;Mazet, Clement
以乙烯基芳烃和异氰酸酯为原料，研究了铜催化的硼化羧酰胺化反应。炔，支链的1，3-二烯，和双环烯烃也被发现是主管耦合合作伙伴。使用手性膦胺配体，开发了这种转化的对映选择性变体，提供了一组具有前所未有的对映选择性水平的α-手性酰胺。通过一系列具有代表性的立体保留后催化衍生化反应，证明了该方法的合成实用性。
A Cu-catalyzed borylative carboxamidation reaction has been developed using vinylarenes and isocyanates. Alkynes, branched 1,3-dienes, and bicyclic alkenes were also found to be competent coupling partners. Using a chiral phosphanamine ligand, an enantioselective variant of this transformation was developed, affording a set of alpha-chiral amides with unprecedented levels of enantioselectivity. The synthetic utility of the method was demonstrated through a series of representative stereoretentive postcatalytic derivatizations.