Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation

[Image: see text] 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 condit...

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Autores principales: Faltracco, Matteo, Cotogno, Silvia, Vande Velde, Christophe M. L., Ruijter, Eelco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6760471/
https://www.ncbi.nlm.nih.gov/pubmed/31446758
http://dx.doi.org/10.1021/acs.joc.9b01994
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author Faltracco, Matteo
Cotogno, Silvia
Vande Velde, Christophe M. L.
Ruijter, Eelco
author_facet Faltracco, Matteo
Cotogno, Silvia
Vande Velde, Christophe M. L.
Ruijter, Eelco
author_sort Faltracco, Matteo
collection PubMed
description [Image: see text] 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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spelling pubmed-67604712019-09-26 Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation Faltracco, Matteo Cotogno, Silvia Vande Velde, Christophe M. L. Ruijter, Eelco J Org Chem [Image: see text] 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. American Chemical Society 2019-08-26 2019-09-20 /pmc/articles/PMC6760471/ /pubmed/31446758 http://dx.doi.org/10.1021/acs.joc.9b01994 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Faltracco, Matteo
Cotogno, Silvia
Vande Velde, Christophe M. L.
Ruijter, Eelco
Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation
title Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation
title_full Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation
title_fullStr Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation
title_full_unstemmed Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation
title_short Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation
title_sort catalytic asymmetric synthesis of diketopiperazines by intramolecular tsuji–trost allylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6760471/
https://www.ncbi.nlm.nih.gov/pubmed/31446758
http://dx.doi.org/10.1021/acs.joc.9b01994
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