Direct Access to Chiral Secondary Amides by Copper-Catalyzed Borylative Carboxamidation of Vinylarenes with Isocyanates

被引：68

作者：

Fiorito, Daniele ^{[1
]}

Liu, Yangbin ^{[1
]}

Besnard, Celine ^{[2
]}

Mazet, Clement ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, 30 Quai Ernest Ansermet, CH-1211 Geneva, Switzerland

[2] Univ Geneva, Lab Crystallog, 24 Quai Ernest Ansermet, CH-1211 Geneva, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 01期

基金：

瑞士国家科学基金会;

关键词：

ASYMMETRIC HYDROBORATION; IN-SITU; CYCLOADDITION; AMIDATION; LIGANDS; ALKENES; AMINOBORATION; ARYLBORATION; CYCLIZATION; 1,3-DIENES;

D O I：

10.1021/jacs.9b12297

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：623 / 632

页数：10

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