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Atroposelective construction of axially chiral enamides via N-allylic alkylation.

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Herein, we report the catalytic asymmetric synthesis of a unique family of axially chiral enamides in good yields with excellent enantioselectivities under mild conditions. These new axially chiral compounds feature… Click to show full abstract

Herein, we report the catalytic asymmetric synthesis of a unique family of axially chiral enamides in good yields with excellent enantioselectivities under mild conditions. These new axially chiral compounds feature a flexible skeleton and a high degree of rotational freedom, which raises difficulties for enantiocontrol. A mechanism model is proposed to interpret the stereoselectivity, in which both the steric difference of the ortho substituents and the π-π stacking interaction may contribute to the stereo-control.

Keywords: construction axially; atroposelective construction; enamides via; via allylic; axially chiral; chiral enamides

Journal Title: Chemical communications
Year Published: 2022

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