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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Main Authors: Ni, Qijian, Xiong, Jiawen, Song, Xiaoxiao, Raabe, Gerhard, Enders, Dieter
Format: Online
Language:English
Published: 2015
Online Access:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4702349/
id pubmed-4702349
recordtype oai_dc
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 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/)
repository_type Open Access Journal
institution_category Foreign Institution
institution US National Center for Biotechnology Information
building NCBI PubMed
collection Online Access
language English
format Online
author Ni, Qijian
Xiong, Jiawen
Song, Xiaoxiao
Raabe, Gerhard
Enders, Dieter
spellingShingle Ni, Qijian
Xiong, Jiawen
Song, Xiaoxiao
Raabe, Gerhard
Enders, Dieter
N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
author_facet Ni, Qijian
Xiong, Jiawen
Song, Xiaoxiao
Raabe, Gerhard
Enders, Dieter
author_sort Ni, Qijian
title 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_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_sort n-heterocyclic carbene catalyzed enantioselective annulation of benzothiazolyl ethyl acetates with 2-bromoenals
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).
publishDate 2015
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4702349/
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