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

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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%… Click to show full 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.

Keywords: addition; carbon quaternary; asymmetric decarboxylative; alkenyl oxindoles; catalytic asymmetric

Journal Title: Organic letters
Year Published: 2022

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