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Faltracco M, Cotogno S, Vande Velde CML, et al. Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation. J Org Chem. 2019;84(18):12058-12070doi: 10.1021/acs.joc.9b01994.
Faltracco, M., Cotogno, S., Vande Velde, C. M. L., & Ruijter, E. (2019). Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation. The Journal of organic chemistry, 84(18), 12058-12070. https://doi.org/10.1021/acs.joc.9b01994
Faltracco, Matteo, et al. "Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation." The Journal of organic chemistry vol. 84,18 (2019): 12058-12070. doi: https://doi.org/10.1021/acs.joc.9b01994
Faltracco M, Cotogno S, Vande Velde CML, Ruijter E. Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation. J Org Chem. 2019 Sep 20;84(18):12058-12070. doi: 10.1021/acs.joc.9b01994. Epub 2019 Sep 10. PMID: 31446758; PMCID: PMC6760471.
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J Org Chem. 2019 Sep 20;84(18):12058-12070. doi: 10.1021/acs.joc.9b01994. Epub 2019 Sep 10.

Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation.

The Journal of organic chemistry

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

Affiliations

  1. Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems (AIMMS) , Vrije Universiteit Amsterdam , De Boelelaan 1108 , 1081 HZ Amsterdam , The Netherlands.
  2. Advanced Reactor Technology, Faculty of Applied Engineering , University of Antwerp , Groenenborgerlaan 171 , 2020 Antwerpen , Belgium.

PMID: 31446758 PMCID: PMC6760471 DOI: 10.1021/acs.joc.9b01994

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.

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