A New Benzotriazole??Mediated Stereoflexible Gateway to Hetero??2, 5??diketopiperazines

…, E Todadze, CV Stevens, AR Katritzky

Index: Monbaliu, Jean-Christophe M.; Hansen, Finn K.; Beagle, Lucas K.; Panzner, Matthew J.; Steel, Peter J.; Todadze, Ekaterina; Stevens, Christian V.; Katritzky, Alan R. Chemistry - A European Journal, 2012 , vol. 18, # 9 p. 2632 - 2638

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Citation Number: 17

Abstract

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- ...