A new semirigid dipeptide mimetic was prepared on multigram scale, in good yield, and in a stereocontrolled way, starting from commercially available and unexpensive reagents, i.e., N-benzylpiperidone, tosyl azide, and proline methyl ester. The optimized multicomponent process consisted of a cascade click cycloaddition and a ring rearrangement reaction, followed by a reductive step. Theoretical calculations were performed to elucidate the reaction mechanism and support the stereochemical outcome of the reduction. Finally, the new scaffold was used for the preparation of model peptidomimetics, whose beta turn conformation was confirmed by dynamic NMR experiments.

Asymmetric Modular Synthesis of a Semirigid Dipeptide Mimetic by Cascade Cycloaddition/Ring Rearrangement and Borohydride Reduction / S. Pellegrino, A. Contini, M.L. Gelmi, L. Lo Presti, R. Soave, E. Erba . - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 79:7(2014 Apr 04), pp. 3094-3102. [10.1021/jo500237j]

Asymmetric Modular Synthesis of a Semirigid Dipeptide Mimetic by Cascade Cycloaddition/Ring Rearrangement and Borohydride Reduction

S. Pellegrino
;
A. Contini;M.L. Gelmi;L. Lo Presti;R. Soave;E. Erba 
Ultimo
2014-04-04

Abstract

A new semirigid dipeptide mimetic was prepared on multigram scale, in good yield, and in a stereocontrolled way, starting from commercially available and unexpensive reagents, i.e., N-benzylpiperidone, tosyl azide, and proline methyl ester. The optimized multicomponent process consisted of a cascade click cycloaddition and a ring rearrangement reaction, followed by a reductive step. Theoretical calculations were performed to elucidate the reaction mechanism and support the stereochemical outcome of the reduction. Finally, the new scaffold was used for the preparation of model peptidomimetics, whose beta turn conformation was confirmed by dynamic NMR experiments.
Conjugate addition-reactions; molecular-energies; click-chemistry; peptidomimetics; mechanism; amidines; model; acids
Settore CHIM/06 - Chimica Organica
Settore CHIM/02 - Chimica Fisica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/238777
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