A new benzotriazole-mediated stereoflexible gateway to hetero-2,5-diketopiperazines

Chemistry : a European Journal
Jean-Christophe M MonbaliuAlan R Katritzky

Abstract

Open chain Cbz-L-aa(1)-L-Pro-Bt (Bt=benzotriazole) sequences were converted into either the corresponding trans- or cis-fused 2,5-diketopiperazines (DKPs) depending on the reaction conditions. Thermodynamic tandem cyclization/epimerization afforded selectively the corresponding trans-DKPs (69-75%). Complementarily, tandem deprotection/cyclization led to the cis-DKPs (65-72%). A representative set of proline-containing cis- and trans-DKPs has been prepared. A mechanistic investigation, based on chiral HPLC, kinetics, and computational studies enabled a rationalization of the results.

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Citations

Jul 21, 2015·The Journal of Organic Chemistry·I WautersC V Stevens
Mar 13, 2015·Organic & Biomolecular Chemistry·Olivier NsengiyumvaAlan R Katritzky
Oct 18, 2012·Chemical Communications : Chem Comm·Jean-Christophe M Monbaliu, Alan R Katritzky
Apr 1, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maria HarizaniEfstathia Ioannou
Sep 15, 2012·Organic & Biomolecular Chemistry·Khanh HaAlan R Katritzky
Feb 12, 2013·Journal of Chemical Theory and Computation·Jean-Christophe M MonbaliuAlan R Katritzky

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