Nickel-Catalyzed Asymmetric Reductive Carbo-Carboxylation of Alkenes with CO 2

Reductive carboxylation of organo (pseudo)halides with CO is a powerful method to provide carboxylic acids quickly. Notably, the catalytic reductive carbo-carboxylation of unsaturated hydrocarbons via CO fixation is a highly challenging but desirable approach for structurally diverse carboxylic acid...

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Veröffentlicht in:Angewandte Chemie International Edition 2021-06, Vol.60 (25), p.14068-14075
Hauptverfasser: Chen, Xiao-Wang, Yue, Jun-Ping, Wang, Kuai, Gui, Yong-Yuan, Niu, Ya-Nan, Liu, Jie, Ran, Chuan-Kun, Kong, Wangqing, Zhou, Wen-Jun, Yu, Da-Gang
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Sprache:eng
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Zusammenfassung:Reductive carboxylation of organo (pseudo)halides with CO is a powerful method to provide carboxylic acids quickly. Notably, the catalytic reductive carbo-carboxylation of unsaturated hydrocarbons via CO fixation is a highly challenging but desirable approach for structurally diverse carboxylic acids. There are only a few reports and no examples of alkenes via transition metal catalysis. We report the first asymmetric reductive carbo-carboxylation of alkenes with CO via nickel catalysis. A variety of aryl (pseudo)halides, such as aryl bromides, aryl triflates and inert aryl chlorides of particular note, undergo the reaction smoothly to give important oxindole-3-acetic acid derivatives bearing a C3-quaternary stereocenter. This transformation features mild reaction conditions, wide substrate scope, facile scalability, good to excellent chemo-, regio- and enantioselectivities. The method highlights the formal synthesis of (-)-Esermethole, (-)-Physostigmine and (-)-Physovenine, and the total synthesis of (-)-Debromoflustramide B, (-)-Debromoflustramine B and (+)-Coixspirolactam A; thereby, opening an avenue for the total synthesis of chiral natural products with CO .
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202102769