Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters

A Ni(ClO(4))(2)-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal C[double bond, length as m-dash]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylk...

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Autores principales: Liu, Ren-Rong, Hu, Jiang-Ping, Hong, Jian-Jun, Lu, Chuan-Jun, Gao, Jian-Rong, Jia, Yi-Xia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5427681/
https://www.ncbi.nlm.nih.gov/pubmed/28553518
http://dx.doi.org/10.1039/c6sc05450a
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author Liu, Ren-Rong
Hu, Jiang-Ping
Hong, Jian-Jun
Lu, Chuan-Jun
Gao, Jian-Rong
Jia, Yi-Xia
author_facet Liu, Ren-Rong
Hu, Jiang-Ping
Hong, Jian-Jun
Lu, Chuan-Jun
Gao, Jian-Rong
Jia, Yi-Xia
author_sort Liu, Ren-Rong
collection PubMed
description A Ni(ClO(4))(2)-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal C[double bond, length as m-dash]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and with excellent enantioselectivities (up to 99%).
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spelling pubmed-54276812017-05-26 Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters Liu, Ren-Rong Hu, Jiang-Ping Hong, Jian-Jun Lu, Chuan-Jun Gao, Jian-Rong Jia, Yi-Xia Chem Sci Chemistry A Ni(ClO(4))(2)-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal C[double bond, length as m-dash]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and with excellent enantioselectivities (up to 99%). Royal Society of Chemistry 2017-04-01 2017-01-19 /pmc/articles/PMC5427681/ /pubmed/28553518 http://dx.doi.org/10.1039/c6sc05450a Text en This journal is © The Royal Society of Chemistry 2017 https://creativecommons.org/licenses/by-nc/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/ (https://creativecommons.org/licenses/by-nc/3.0/) ) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Liu, Ren-Rong
Hu, Jiang-Ping
Hong, Jian-Jun
Lu, Chuan-Jun
Gao, Jian-Rong
Jia, Yi-Xia
Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
title Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
title_full Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
title_fullStr Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
title_full_unstemmed Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
title_short Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
title_sort enantioselective [2 + 2] cycloaddition of n-allenamides with cyclic n-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5427681/
https://www.ncbi.nlm.nih.gov/pubmed/28553518
http://dx.doi.org/10.1039/c6sc05450a
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