Asymmetric Benzylic Allylic Alkylation Reaction of 3-Furfural Derivatives by Dearomatizative Dienamine Activation

Chemistry : a European Journal
Xiao-Long HeYing-Chun Chen

Abstract

The dearomatizative dienamine-type ortho-quinodimethane species are smoothly generated between 2-alkyl-3-furfurals and chiral secondary amine catalysts, which undergo asymmetric benzylic allylic alkylation reactions with 2-nitroallylic acetates efficiently. A spectrum of densely functionalized 3-furfural derivatives are delivered in moderate to high yields with good to excellent diastereo- and enantioselectivity (up to 98 % yield, >19:1 d.r., >99 % ee). The latent transformations allow the facile production of some enantioenriched architectures, such as 1,1,2,2-tetraarylethanes and triarylmethanes, which are not easily available from other protocols.

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Citations

Aug 16, 2018·Chemistry : a European Journal·Ben-Xian XiaoYing-Chun Chen
Aug 21, 2018·Angewandte Chemie·Artur PrzydaczŁukasz Albrecht
Jan 9, 2020·Organic & Biomolecular Chemistry·Milanpreet Kaur, Jeffrey F Van Humbeck

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