Catalytic, Enantioselective Mukaiyama Aldol Addition Reaction: The Development of Chiral Ti (IV) Complexes with Tri-and Tetra-dentate Ligands

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The focus of this research is the use of Ti(IV) complexes containing Schiff-base tridentate ligands to carry out enantioselective aldol additions. Ligands will be based upon 2-amino-2'-hydroxy-1,1'-binapthyl and 2,2'-diaminobinapthyl scaffolds upon which the the counterion and nature of the salicylimine are varied. Enantioselective aldol addition reactions of acetate, propionate, crotonate and ketone derived silyl enol ethers will be explored. The catalytic methodology will lead to the production of optically active beta-hydroxy esters and delta-hydroxy-alpha, beta-unsaturated esters. With this award, the Synthetic Organic Program is supporting the research of Dr. Erick M. Carreira of the Department of Chemistry at the Califonia Institute of Technology. Professor Carreira will focus his work on the development of catalytic methodology for the the formation of carbon-carbon bonds. The optically active products are useful intermediates for the preparation of stereochemically complex systems that have important biological properties.