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Catalytic Asymmetric Michael Addition Reactions of Metal Pyrrolates : New Methodology and Synthetic Applications

Objective

Alkali metal pyrrolate derivatives are effective /V-centred nucleophiles that partake in Michael addition reactions to electron poor alkenes. In the former case, the reaction leads to masked ÿ-amino acids that may be converted to the parent amino compound through a tandem ozonolysis/acid hydrolysis procedure. The reactions may be made asymmetric by using covalently linked chirality on the 2-position of the pyrrole ring, or catalytic quantities of chiral multidentate ligands to accelerate the Michael additio n reaction. We wish to explore and develop these ideas in the hope of securing the most scalable asymmetric route to ÿ-amino acids to date. The proposed chemistry falls into the class of asymmetric nucleophilic catalysis - no toxic transition metals are us ed and the reactions should be efficient and clean. The developed catalytic asymmetric reaction will be investigated to probe the scope of the chemistry and then applied to the synthesis of biologically important and/or naturally occurring natural products . Additionally the stereoselective enolate chemistry at the a-centre of the Michael adducts will be probed. With emphasis on the stereoselectivity in the chemistry and the diversity of functionality that enolate chemistry can bring to the Michael adducts, we will investigate the wealth of structural complexity we can create. This will add value to the utility of the products and the methodology as a whole.

Call for proposal

FP6-2002-MOBILITY-5
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Funding Scheme

EIF - Marie Curie actions-Intra-European Fellowships

Coordinator

THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF CAMBRIDGE
Address
The Old Schools, Trinity Lane
Cambridge
United Kingdom