The use of solid-supported catalysts has several advantages over traditional homogeneous reactions such as easy product purification, the possibility of catalyst recycling and the potential of flow chemistry applications. Our group has recently developed a novel class of highly active, bifunctional iminophosphorane organocatalysts and described their application in the asymmetric nitro-Mannich reaction of phosphoryl ketimines.1 The synthesis of these catalysts through the coupling of a triarylphosphine and a chiral azide to form the active iminophosphorane allows for simultaneous catalyst formation and immobilization through the use of polystyrene-supported triphenylphosphine as one of the coupling partners. This circumvents the need for any additional synthetic steps to form a tether to immobilize the catalyst.The polystyrene-supported bifunctional iminophosphorane catalyst has been successfully applied to the asymmetric nitro-Mannich reaction of phosphoryl ketimines and the asymmetric addition of substituted alkylmalonates and keto-amides to nitrostyrene. The products are obtained in good to excellent yield and enantiomeric excess. Neither the enantiomeric excess nor the reaction rate of these reactions are eroded by the immobilization of the catalyst. Furthermore, catalyst recycling and application in a solid phase reactor in a flow chemistry system have been demonstrated.1J. Am. Chem. Soc. 2013 , 135, 16348�16351 Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/241nm/uploads/61126_untitled.jpg' alt='' />

Development and application of a highly active, polystyrene-supported bifunctional iminophosphorane organocatalyst

248th National Meeting (2014)

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