Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage

An enantioselective [3 + 2] annulation of donor–acceptor aziridines with aldehydes has been realized using a Nd(OTf)(3)/N,N′-dioxide/LiNTf(2) catalyst system, providing various chiral cis-1,3-oxazolidines in moderate to good yields with high levels of stereocontrol. A relay catalytic process is prop...

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Detalles Bibliográficos
Autores principales: Liao, Yuting, Liu, Xiaohua, Zhang, Yu, Xu, Yali, Xia, Yong, Lin, Lili, Feng, Xiaoming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6013814/
https://www.ncbi.nlm.nih.gov/pubmed/30155018
http://dx.doi.org/10.1039/c5sc04151a
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author Liao, Yuting
Liu, Xiaohua
Zhang, Yu
Xu, Yali
Xia, Yong
Lin, Lili
Feng, Xiaoming
author_facet Liao, Yuting
Liu, Xiaohua
Zhang, Yu
Xu, Yali
Xia, Yong
Lin, Lili
Feng, Xiaoming
author_sort Liao, Yuting
collection PubMed
description An enantioselective [3 + 2] annulation of donor–acceptor aziridines with aldehydes has been realized using a Nd(OTf)(3)/N,N′-dioxide/LiNTf(2) catalyst system, providing various chiral cis-1,3-oxazolidines in moderate to good yields with high levels of stereocontrol. A relay catalytic process is proposed where LiNTf(2) promotes the formation of azomethine ylide intermediates, and a chiral Nd(iii)–N,N′-dioxide complex accelerates the asymmetric cycloaddition.
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spelling pubmed-60138142018-08-28 Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage Liao, Yuting Liu, Xiaohua Zhang, Yu Xu, Yali Xia, Yong Lin, Lili Feng, Xiaoming Chem Sci Chemistry An enantioselective [3 + 2] annulation of donor–acceptor aziridines with aldehydes has been realized using a Nd(OTf)(3)/N,N′-dioxide/LiNTf(2) catalyst system, providing various chiral cis-1,3-oxazolidines in moderate to good yields with high levels of stereocontrol. A relay catalytic process is proposed where LiNTf(2) promotes the formation of azomethine ylide intermediates, and a chiral Nd(iii)–N,N′-dioxide complex accelerates the asymmetric cycloaddition. Royal Society of Chemistry 2016-06-01 2016-02-23 /pmc/articles/PMC6013814/ /pubmed/30155018 http://dx.doi.org/10.1039/c5sc04151a Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Liao, Yuting
Liu, Xiaohua
Zhang, Yu
Xu, Yali
Xia, Yong
Lin, Lili
Feng, Xiaoming
Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage
title Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage
title_full Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage
title_fullStr Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage
title_full_unstemmed Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage
title_short Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage
title_sort asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6013814/
https://www.ncbi.nlm.nih.gov/pubmed/30155018
http://dx.doi.org/10.1039/c5sc04151a
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