N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals

An N-heterocyclic carbene catalyzed enantioselective [3+3] annulation of benzothiazolyl acetates with 2-bromoenals has been developed. The protocol provides a direct asymmetric synthesis of dihydro-1H-benzothiazolopyridinones in good to very good yields and medium ee values. In many cases, the virtu...

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Detalles Bibliográficos
Autores principales: Ni, Qijian, Xiong, Jiawen, Song, Xiaoxiao, Raabe, Gerhard, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4702349/
https://www.ncbi.nlm.nih.gov/pubmed/26752810
http://dx.doi.org/10.1055/s-0034-1381004
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author Ni, Qijian
Xiong, Jiawen
Song, Xiaoxiao
Raabe, Gerhard
Enders, Dieter
author_facet Ni, Qijian
Xiong, Jiawen
Song, Xiaoxiao
Raabe, Gerhard
Enders, Dieter
author_sort Ni, Qijian
collection PubMed
description An N-heterocyclic carbene catalyzed enantioselective [3+3] annulation of benzothiazolyl acetates with 2-bromoenals has been developed. The protocol provides a direct asymmetric synthesis of dihydro-1H-benzothiazolopyridinones in good to very good yields and medium ee values. In many cases, the virtually enantiopure heterocycles are available through a single recrystallization (99% ee).
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spelling pubmed-47023492016-01-06 N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals Ni, Qijian Xiong, Jiawen Song, Xiaoxiao Raabe, Gerhard Enders, Dieter Synlett Article An N-heterocyclic carbene catalyzed enantioselective [3+3] annulation of benzothiazolyl acetates with 2-bromoenals has been developed. The protocol provides a direct asymmetric synthesis of dihydro-1H-benzothiazolopyridinones in good to very good yields and medium ee values. In many cases, the virtually enantiopure heterocycles are available through a single recrystallization (99% ee). 2015-06-11 /pmc/articles/PMC4702349/ /pubmed/26752810 http://dx.doi.org/10.1055/s-0034-1381004 Text en License terms: CC BY-NC-ND (http://creativecommons.org/licenses/by-nc-nd/4.0/)
spellingShingle Article
Ni, Qijian
Xiong, Jiawen
Song, Xiaoxiao
Raabe, Gerhard
Enders, Dieter
N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
title N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
title_full N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
title_fullStr N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
title_full_unstemmed N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
title_short N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
title_sort n-heterocyclic carbene catalyzed enantioselective annulation of benzothiazolyl ethyl acetates with 2-bromoenals
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4702349/
https://www.ncbi.nlm.nih.gov/pubmed/26752810
http://dx.doi.org/10.1055/s-0034-1381004
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