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Atroposelective Catalytic Asymmetric Allylic Alkylation Reaction for Axially Chiral Anilides with Achiral Morita–Baylis–Hillman Carbonates

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posted on 18.09.2018, 00:00 authored by Shou-Lei Li, Chen Yang, Quan Wu, Han-Liang Zheng, Xin Li, Jin-Pei Cheng
A highly efficient method to access axially chiral anilides through asymmetric allylic alkylation reaction with achiral Morita–Baylis–Hillman carbonates by using a biscinchona alkaloid catalyst was reported. Through the atroposelective approach, a broad range of axially chiral anilide products with different acyl groups, such as substituted phenyl, naphthyl, alkyl, enyl, styryl, and benzyl, were generated with very good yields, moderate to excellent cis:trans ratios, and good to excellent enantioselectivities. The reaction can be scaled up, and the synthetic utility of axially chiral anilides was proved by transformations. Moreover, the linear free energy relationship analysis was introduced to investigate the reaction.