Palladium-Catalyzed Cascade C-H Functionalization/Asymmetric Allylation Reaction of Aryl α-Diazoamides and Allenes: Lewis Acid Makes a Difference.

Min-Song Wu, Xiao-Yun Ruan, Zhi-Yong Han, Liu-Zhu Gong

Chemistry (Weinheim an der Bergstrasse, Germany) 2022 Feb 19

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A Pd-catalyzed cascade C-H functionalization/asymmetric allylation reaction with aryl α-diazoamides and allenes has been developed. The reaction provides an efficient approach to construct chiral 3,3-disubstituted oxindole derivatives in high levels of yield and enantioselectivity (up to 93 % ee). Notably, the chromium complex works as Lewis acid to facilitate the formation of palladium carbene and to enhance acidity of carboxylic acid, allowing for higher stereochemical control and efficiency. © 2022 Wiley-VCH GmbH.

Citation

Min-Song Wu, Xiao-Yun Ruan, Zhi-Yong Han, Liu-Zhu Gong. Palladium-Catalyzed Cascade C-H Functionalization/Asymmetric Allylation Reaction of Aryl α-Diazoamides and Allenes: Lewis Acid Makes a Difference. Chemistry (Weinheim an der Bergstrasse, Germany). 2022 Feb 19;28(11):e202104218