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Catalytic Asymmetric Decarboxylative Michael Addition To Construct an All-Carbon Quaternary Center with 3-Alkenyl-oxindoles. | LitMetric

Catalytic Asymmetric Decarboxylative Michael Addition To Construct an All-Carbon Quaternary Center with 3-Alkenyl-oxindoles.

Org Lett

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemitry and Chemical Engneeng, Shihezi University, Xinjiang Uygur Autonomous Region 832000, People's Republic of China.

Published: April 2022


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Article Abstract

The first highly enantioselective asymmetric decarboxylative addition of β-keto acids with 3-alkenyl-oxindoles bearing an all-carbon quaternary stereocenter have been developed. The relevant products were acquired in 49-98% yields with 88-98% enantioselectivities in the presence of 0.04-1.0 mol % of chiral rhodium catalyst. The comprehensive practicability of this method was proven in the preparation of the key intermediate, which can be easily transformed into analogues of physovenine and physostigmine.

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http://dx.doi.org/10.1021/acs.orglett.2c00411DOI Listing

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