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Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence
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Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence
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Journal Article
Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence
2019
Overview
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.
Catalytic asymmetric dearomatization (CADA) reactions readily convert common aromatic compounds to diverse 3D chiral, polycyclic molecules. Here, the authors report an intermolecular asymmetric dearomatization of nucleophile-tethered α-naphthols affording functionalized cyclic ketones with high enantioselectivity.
