PROJECT SUMMARY/ABSTRACT This proposal will elucidate the various steric and electronic parameters of a P-catalyst necessary for enantioinduction in tandem amidation/amide functionalizations through deoxygenative P(III)/P(V) catalysis; an important transformation for the synthesis of biologically active compounds. This proposal will first examine P- catalyzed enantioselective amidations, followed by P-catalyzed enantioretentive amide functionalizations. Finally, these catalysts will be combined for a one-pot synthesis of enantioenriched secondary nitriles from racemic carboxylic acids, a moiety important to the pharmaceutical community. Overall, during this fellowship period I seek to gain expertise in inorganic main-group chemistry, including computational analyses and modern inorganic synthetic techniques. Such skills will complement my existing skillset, creating a strong foundation in catalyst design for my future career goals.

PROJECT NARRATIVE This proposal will determine the various steric and electronic factors in designing stereoselective phosphorous catalysts for enantioselective acylations and tandem functionalizations. This proposal hypothesizes new, electron rich chiral P-catalysts which can function as a stereocontrolling element during several P-catalyzed steps. This proposal will use these catalysts for chemoselective P-catalysed dehydrative nitrile formation, an important transformation to the pharmaceutical community.