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 language | English |
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Pages (from-to) | 12058-12070 |
Number of pages | 13 |
Journal | The Journal of organic chemistry |
Volume | 84 |
Issue number | 18 |
Early online date | 26 Aug 2019 |
DOIs | |
Publication status | Published - 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.
Funders | Funder number |
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3D Structural Platform Aiming for Chemical Excellence | |
Hercules Foundation | AUGE/11/029 |
Nederlandse Organisatie voor Wetenschappelijk Onderzoek | |
Universiteit Gent |
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CCDC 1902629: Experimental Crystal Structure Determination
Faltracco, M. (Contributor), Cotogno, S. (Contributor), Velde, C. M. L. V. (Contributor) & Ruijter, E. (Contributor), Unknown Publisher, 20 Sept 2019
DOI: 10.5517/ccdc.csd.cc21vv4x, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21vv4x&sid=DataCite
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