Journal
NATURE COMMUNICATIONS
Volume 10, Issue -, Pages -Publisher
NATURE RESEARCH
DOI: 10.1038/s41467-019-11109-9
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Funding
- Ministry of Science and Technology of China [2016YFA0202900]
- National Natural Science Foundation of China [21772219, 21821002]
- Science and Technology Commission of Shanghai Municipality [16XD1404300, 18QA1404900, 16490712200]
- Chinese Academy of Sciences [XDB20000000, QYZDYSSWSLH012]
- Youth Innovation Promotion Association of CAS [2017302]
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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 alpha-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.
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