A New Benzotriazole‐Mediated Stereoflexible Gateway to Hetero‐2,5‐diketopiperazines | Zendy

Monbaliu JeanChristophe M. | Zendy; Hansen Finn K. | Zendy; Beagle Lucas K. | Zendy; Panzner Matthew J. | Zendy; Steel Peter J. | Zendy; Todadze Ekaterina | Zendy; Stevens Christian V. | Zendy; Katritzky Alan R. | Zendy

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

Author(s) -

Monbaliu JeanChristophe M.,

Hansen Finn K.,

Beagle Lucas K.,

Panzner Matthew J.,

Steel Peter J.,

Todadze Ekaterina,

Stevens Christian V.,

Katritzky Alan R.

Publication year - 2012

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201103143

Subject(s) - diketopiperazines , chemistry , benzotriazole , tandem , epimer , kinetics , combinatorial chemistry , stereochemistry , organic chemistry , materials science , physics , quantum mechanics , composite material

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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