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Issue 68, 2014
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Diastereoselective synthesis of novel aza-diketopiperazines via a domino cyclohydrocarbonylation/addition process

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Abstract

Herein, we report an unprecedented, short and diastereo-selective synthesis of newly reported aza-diketopiperazine (aza-DKP) scaffolds starting from amino acids. The strategy is based on a Rh(I)-catalyzed hydroformylative cyclohydrocarbonylation of allyl-substituted aza-DKP, followed by a diastereoselective functionalization of the platform. This methodology allows the synthesis of novel bicyclic and tricyclic aza-DKP scaffolds incorporating six- or seven-membered rings, with potential applications in medicinal chemistry.

Graphical abstract: Diastereoselective synthesis of novel aza-diketopiperazines via a domino cyclohydrocarbonylation/addition process

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Supplementary files

Article information


Submitted
14 May 2014
Accepted
03 Jul 2014
First published
04 Jul 2014

This article is Open Access

Chem. Commun., 2014,50, 9657-9660
Article type
Communication
Author version available

Diastereoselective synthesis of novel aza-diketopiperazines via a domino cyclohydrocarbonylation/addition process

P. Regenass, J. Margathe, A. Mann, J. Suffert, M. Hibert, N. Girard and D. Bonnet, Chem. Commun., 2014, 50, 9657
DOI: 10.1039/C4CC03660C

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