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

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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… Click to show full 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.

Keywords: azonaphthalene pyrazolone; asymmetric synthesis; pyrazole; reaction azonaphthalene

Journal Title: Chemical communications
Year Published: 2019

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