Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides

A dipeptide-based urea-amide tertiary amine (DP-UAA) was shown to be an effective Brønsted base catalyst for the first asymmetric annulation reaction between 5H-thiazol-4-ones and N-itaconimides. High levels of enantioselectivity (up to 99% ee) and diastereoselectivity (>19:1 dr) were obtained fo...

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Detalles Bibliográficos
Autores principales: Qiu, Shuai, Tan, Choon-Hong, Jiang, Zhiyong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238619/
https://www.ncbi.nlm.nih.gov/pubmed/28144296
http://dx.doi.org/10.3762/bjoc.12.222
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author Qiu, Shuai
Tan, Choon-Hong
Jiang, Zhiyong
author_facet Qiu, Shuai
Tan, Choon-Hong
Jiang, Zhiyong
author_sort Qiu, Shuai
collection PubMed
description A dipeptide-based urea-amide tertiary amine (DP-UAA) was shown to be an effective Brønsted base catalyst for the first asymmetric annulation reaction between 5H-thiazol-4-ones and N-itaconimides. High levels of enantioselectivity (up to 99% ee) and diastereoselectivity (>19:1 dr) were obtained for a series of spirocyclic 1,4-sulfur-bridged piperidinone-based succinimides.
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spelling pubmed-52386192017-01-31 Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides Qiu, Shuai Tan, Choon-Hong Jiang, Zhiyong Beilstein J Org Chem Full Research Paper A dipeptide-based urea-amide tertiary amine (DP-UAA) was shown to be an effective Brønsted base catalyst for the first asymmetric annulation reaction between 5H-thiazol-4-ones and N-itaconimides. High levels of enantioselectivity (up to 99% ee) and diastereoselectivity (>19:1 dr) were obtained for a series of spirocyclic 1,4-sulfur-bridged piperidinone-based succinimides. Beilstein-Institut 2016-11-01 /pmc/articles/PMC5238619/ /pubmed/28144296 http://dx.doi.org/10.3762/bjoc.12.222 Text en Copyright © 2016, Qiu et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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 Full Research Paper
Qiu, Shuai
Tan, Choon-Hong
Jiang, Zhiyong
Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides
title Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides
title_full Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides
title_fullStr Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides
title_full_unstemmed Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides
title_short Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides
title_sort highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5h-thiazol-4-ones with n-itaconimides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238619/
https://www.ncbi.nlm.nih.gov/pubmed/28144296
http://dx.doi.org/10.3762/bjoc.12.222
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