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镍/光催化不对称烯丙基羰基氨化反应。

Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes.

机构信息

Hefei National Laboratory for Physical Science at the Microscale, Department of Chemistry, Center for Excellence in Molecular Synthesis , University of Science and Technology of China , Hefei , Anhui 230026 , P. R. China.

出版信息

J Am Chem Soc. 2020 Feb 5;142(5):2180-2186. doi: 10.1021/jacs.9b12554. Epub 2020 Jan 27.

Abstract

An unprecedented asymmetric acyl-carbamoylation of pendant alkenes tethered on aryl carbamic chlorides with both aliphatic and aromatic aldehydes has been developed via the cooperative catalysis of a chiral nickel-PHOX complex and tetrabutylammonium decatungstate. This reaction represents the first example of merging hydrogen-atom-transfer photochemistry and asymmetric transition metal catalysis in difunctionalization of alkenes. Using this protocol, a variety of oxindoles bearing a challenging quaternary stereogenic center are furnished under mild conditions in highly enantioselective manner.

摘要

通过手性镍-PHOX 配合物和四丁基铵十钨酸盐的协同催化,发展了一种前所未有的芳基碳氨氯上连接的烯丙基烯烃与脂肪族和芳香族醛的不对称酰基氨甲酰化反应。该反应代表了在烯烃双官能化中合并氢原子转移光化学和不对称过渡金属催化的第一个例子。使用该方案,在温和条件下以高度对映选择性的方式提供了多种带有挑战性的季立体中心的氧化吲哚。

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