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Over the past decade many bifunctional amine-thioureas have been developed as active metal-free organocatalysts.Cooperative catalysis of these amino-thioureas allows high reaction rates and excellent transfer of stereochemical information.Despite these impressive advances,the design of new high-performance catalysts for applications in asymmetric catalytic reactions is of ongoing interest in organic chemistry.Herein we describe a cooperative catalyst system consisting of a chiral aminethiourea and an achiral organic acid that promotes the conjugate addition of 4-nonsubstituted pyrazolones to nitroolefins and subsequent dearomative chlorination.The corresponding adducts and the subsequent products were obtained in high to excellent yields(up to 99%)and high stereoselectivities(up to 99/1 dr,98%ee)under mild reaction conditions.These transformations provide an easy access to enantio-enriched pyrazole derivatives,which could possess potential pharmaceutical activity.
Over the past decade many bifunctional amine-thioureas have been developed as active metal-free organocatalysts. Cooperative catalysis of these amino-thioureas allows high reaction rates and excellent transfer of stereochemical information. Abstract these impressive advances, the design of new high-performance catalysts for applications in asymmetric catalytic reactions is of ongoing interest in organic chemistry. Herein we describe a cooperative catalyst system consisting of a chiral amine thiourea and an achiral organic acid that promotes the conjugate addition of 4-nonsubstituted pyrazolones to nitroolefins and subsequent dearomative chlorination. adducts and the subsequent products were obtained in high to excellent yields (up to 99%) and high stereoselectivities (up to 99/1 dr, 98% ee) under mild reaction conditions .sese transformations provide an easy access to enantio-enriched pyrazole derivatives , which could possess potential pharmaceutical activity.