Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides

We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman (MBH) carbonates with maleimides, which can efficiently construct functionalized cyclopentenes bearing three contiguous stereocenters in moderate to excellent yields and excellent...

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Detalles Bibliográficos
Autores principales: Deng, Hong-Ping, Wang, De, Wei, Yin, Shi, Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458726/
https://www.ncbi.nlm.nih.gov/pubmed/23019436
http://dx.doi.org/10.3762/bjoc.8.121
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author Deng, Hong-Ping
Wang, De
Wei, Yin
Shi, Min
author_facet Deng, Hong-Ping
Wang, De
Wei, Yin
Shi, Min
author_sort Deng, Hong-Ping
collection PubMed
description We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman (MBH) carbonates with maleimides, which can efficiently construct functionalized cyclopentenes bearing three contiguous stereocenters in moderate to excellent yields and excellent diastereo- and enantioselectivities. A plausible mechanism has been also proposed on the basis of control experiments and previous literature.
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spelling pubmed-34587262012-09-27 Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides Deng, Hong-Ping Wang, De Wei, Yin Shi, Min Beilstein J Org Chem Letter We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman (MBH) carbonates with maleimides, which can efficiently construct functionalized cyclopentenes bearing three contiguous stereocenters in moderate to excellent yields and excellent diastereo- and enantioselectivities. A plausible mechanism has been also proposed on the basis of control experiments and previous literature. Beilstein-Institut 2012-07-16 /pmc/articles/PMC3458726/ /pubmed/23019436 http://dx.doi.org/10.3762/bjoc.8.121 Text en Copyright © 2012, Deng et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Deng, Hong-Ping
Wang, De
Wei, Yin
Shi, Min
Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides
title Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides
title_full Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides
title_fullStr Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides
title_full_unstemmed Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides
title_short Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides
title_sort chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of morita–baylis–hillman carbonates with maleimides
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458726/
https://www.ncbi.nlm.nih.gov/pubmed/23019436
http://dx.doi.org/10.3762/bjoc.8.121
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