Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines

A highly diastereoselective cyclopropanation of cyclic enones with sulfur ylides was developed under catalyst-free conditions, producing multifunctional spirocyclopropanes in generally excellent yields (up to 99% yield and >99:1 d.r.). The asymmetric version of this method was realized by using a...

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Autores principales: Li, Yi, Li, Qing-Zhu, Huang, Li, Liang, Hong, Yang, Kai-Chuan, Leng, Hai-Jun, Liu, Yue, Shen, Xu-Dong, Gou, Xiao-Jun, Li, Jun-Long
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155796/
https://www.ncbi.nlm.nih.gov/pubmed/28241452
http://dx.doi.org/10.3390/molecules22020328
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author Li, Yi
Li, Qing-Zhu
Huang, Li
Liang, Hong
Yang, Kai-Chuan
Leng, Hai-Jun
Liu, Yue
Shen, Xu-Dong
Gou, Xiao-Jun
Li, Jun-Long
author_facet Li, Yi
Li, Qing-Zhu
Huang, Li
Liang, Hong
Yang, Kai-Chuan
Leng, Hai-Jun
Liu, Yue
Shen, Xu-Dong
Gou, Xiao-Jun
Li, Jun-Long
author_sort Li, Yi
collection PubMed
description A highly diastereoselective cyclopropanation of cyclic enones with sulfur ylides was developed under catalyst-free conditions, producing multifunctional spirocyclopropanes in generally excellent yields (up to 99% yield and >99:1 d.r.). The asymmetric version of this method was realized by using an easily available chiral sulfur ylide, affording products with moderate to good stereoselectivity.
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spelling pubmed-61557962018-11-13 Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines Li, Yi Li, Qing-Zhu Huang, Li Liang, Hong Yang, Kai-Chuan Leng, Hai-Jun Liu, Yue Shen, Xu-Dong Gou, Xiao-Jun Li, Jun-Long Molecules Article A highly diastereoselective cyclopropanation of cyclic enones with sulfur ylides was developed under catalyst-free conditions, producing multifunctional spirocyclopropanes in generally excellent yields (up to 99% yield and >99:1 d.r.). The asymmetric version of this method was realized by using an easily available chiral sulfur ylide, affording products with moderate to good stereoselectivity. MDPI 2017-02-22 /pmc/articles/PMC6155796/ /pubmed/28241452 http://dx.doi.org/10.3390/molecules22020328 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Li, Yi
Li, Qing-Zhu
Huang, Li
Liang, Hong
Yang, Kai-Chuan
Leng, Hai-Jun
Liu, Yue
Shen, Xu-Dong
Gou, Xiao-Jun
Li, Jun-Long
Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines
title Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines
title_full Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines
title_fullStr Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines
title_full_unstemmed Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines
title_short Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines
title_sort diastereoselective synthesis of spirocyclopropanes under mild conditions via formal [2 + 1] cycloadditions using 2,3-dioxo-4-benzylidene-pyrrolidines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155796/
https://www.ncbi.nlm.nih.gov/pubmed/28241452
http://dx.doi.org/10.3390/molecules22020328
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