One‐Pot Catalytic Enantioselective Synthesis of 2‐Pyrazolines

A scalable, one‐pot, enantioselective catalytic synthesis of 2‐pyrazolines from beta‐substituted enones and hydrazines is described. Pivoting on a two stage catalytic Michael addition / condensation strategy, the use of an aldehyde to generate a suitable hydrazone derivative of the hydrazine was found to be key for curtailing background reactivity and tuning the catalyst‐controlled enantioselectivity. The new synthetic protocol is easy to perform, uses a new and readily prepared cinchona‐derived bifunctional catalyst, is broad in scope, and tolerates a range of functionalities with high enantioselectivity (up to >99:1 er). The significant scalability of this methodology has been demonstrated with the synthesis of >80 grams of a pyrazoline product with 89% catalyst recovery.

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