Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation

Matteo Faltracco, Silvia Cotogno, Christophe M.L. Vande Velde, Eelco Ruijter

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

We report the intramolecular Tsuji-Trost reaction of Ugi adducts to give spiro-diketopiperazines in high yield and with high enantioselectivity. This approach allows the catalytic asymmetric construction of a broad range of these medicinally important heterocycles under mild conditions, in two steps from cheap, commercially available starting materials.

Original languageEnglish
Pages (from-to)12058-12070
Number of pages13
JournalThe Journal of organic chemistry
Volume84
Issue number18
Early online date26 Aug 2019
DOIs
Publication statusPublished - 20 Sept 2019

Funding

This work was supported by the Netherlands Organisation for Scientific Research (NWO). We thank Ellymay Goossens for the synthesis of some racemic standards, Elwin Janssen for NMR support, and Daniel Preschel for HRMS measurements (all VUA). We also thank Kristof Van Hecke (Ghent University) for providing diffractometer time, and the Hercules Foundation (project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) for funding of the diffractometer.

FundersFunder number
3D Structural Platform Aiming for Chemical Excellence
Hercules FoundationAUGE/11/029
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Universiteit Gent

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