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Poly-functionalised organolithiums: new methods for stability determination and synthetic applications


A great deal of research has been devoted to the development of highly functionalized chiral organometallic reagents because their reaction with organic electrophiles provide an expeditive access to numerous polyfunctional molecules of interest in natural product synthesis and development of new pharmaceuticals.

The stereoselective formation of a new carbon-carbon bond implies the availability of CSp³-hybridized organometallic compounds having a defined configuration. In this sense, alfa-oxy and alfa-aminoor ganolithiums have gained considerably synthetic status due to their configurational stability.

This proposal deals with the study of several aspects of the chemistry of more functionalized alfa-oxy and alfa-aminoorganolithiums, in particular compounds possessing a leaving group (RO-, R2N-) beta to the anionic centre, namely, their stability, aggregation states, reactivity and applications in organic synthesis.

We propose to establish a scale of relative stabilities of highly basic beta-heterosubstituted alfa -oxy and alfa-aminoorganolithiums by developing some new methods for the determination of their pKs, as well as for the establishment of the nature of their aggregation states in solution.

The measurements of pKs will be performed by studying Sn-Li exchange equilibriums.We plan to analyze the aggregation states by DOSY experiments of 1H-NMR, and also perform theoretical DFT calculations. This methodology will allow us to estimate the contribution of the substituent effects, the interaction with the solvent and the nature of the aggregation to the stability and reactivity of these systems.

The results obtained will constitute a tool to rationalize and design new stable polyfunctionalized organolitium systems of increased synthetic value, with application in the synthesis of HIV-1 protease inhibitiors

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