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

Xiao‐Long He; Hui‐Ru Zhao; Chuan‐Qi Duan; Xu Han; Wei Du; Ying‐Chun Chen

Index: 10.1002/chem.201800585

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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.