Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence

Zi-Lei Xia, Chao Zheng (), Ren-Qi Xu and Shu-Li You ()
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Zi-Lei Xia: Chinese Academy of Sciences
Chao Zheng: Chinese Academy of Sciences
Ren-Qi Xu: Chinese Academy of Sciences
Shu-Li You: Chinese Academy of Sciences

Nature Communications, 2019, vol. 10, issue 1, 1-7

Abstract: Abstract Asymmetric dearomatization reactions have recently emerged as a powerful tool for the rapid build-up of the molecular complexity. Chiral three-dimensional polycyclic molecules bearing contiguous stereogenic centers can be synthesized from readily available planar aromatic feedstocks. Here we report that an intermolecular asymmetric dearomatization reaction of α-naphthols bearing a tethered nucleophile at the C4 position of the naphthol ring is achieved by a chiral phosphoric acid. The reaction proceeds via a highly chemo- and regioselective aminative dearomatization/Michael addition sequence, affording a wide array of functionalized cyclic ketones in good yields (up to 93%) with excellent enantioselectivity (up to >99% ee). The catalyst loading can be reduced to 0.1 mol%. Preliminary mechanistic investigations identify that the enantioselectivity is established in the dearomatization step, while the Michael addition is the rate-limiting step. A working model accounting for the origin of the stereochemistry is proposed based on DFT calculations.

Date: 2019
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DOI: 10.1038/s41467-019-11109-9

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