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Asymmetric synthesis of atropisomeric pyrazole via an enantioselective reaction of azonaphthalene with pyrazolone

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Abstract

The first catalytic asymmetric reaction of azonaphthalene with pyrazolone has been established. A wide range of axially chiral pyrazole derivatives have been achieved in good yields (68–99%) with excellent enantioselectivities (83–98% ee) by utilizing chiral phosphoric acid as a catalyst. This strategy provides an efficient and facile approach for the construction of axially chiral pyrazole derivatives. Theoretical calculations were carried out to elucidate the origins of enantioselectivity.

Graphical abstract: Asymmetric synthesis of atropisomeric pyrazole via an enantioselective reaction of azonaphthalene with pyrazolone

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Publication details

The article was received on 16 Aug 2019, accepted on 30 Sep 2019 and first published on 30 Sep 2019


Article type: Communication
DOI: 10.1039/C9CC06360A
Chem. Commun., 2019, Advance Article

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    Asymmetric synthesis of atropisomeric pyrazole via an enantioselective reaction of azonaphthalene with pyrazolone

    H. Yuan, Y. Li, H. Zhao, Z. Yang, X. Li and W. Li, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06360A

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