Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene

A chiral Lewis acid-promoted enantioselective cyclopropanation using phenyliodonium ylide as the carbene precursor was developed. A variety of spirocyclopropane-oxindoles with contiguous tertiary and all carbon quaternary centers were obtained in excellent outcomes (up to 99% yield, >19 : 1 d.r.,...

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Autores principales: Guo, Jing, Liu, Yangbin, Li, Xiangqiang, Liu, Xiaohua, 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/PMC5477038/
https://www.ncbi.nlm.nih.gov/pubmed/28660046
http://dx.doi.org/10.1039/c5sc03658e
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author Guo, Jing
Liu, Yangbin
Li, Xiangqiang
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
author_facet Guo, Jing
Liu, Yangbin
Li, Xiangqiang
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
author_sort Guo, Jing
collection PubMed
description A chiral Lewis acid-promoted enantioselective cyclopropanation using phenyliodonium ylide as the carbene precursor was developed. A variety of spirocyclopropane-oxindoles with contiguous tertiary and all carbon quaternary centers were obtained in excellent outcomes (up to 99% yield, >19 : 1 d.r., up to 99% ee). EPR spectroscopy study supported a stepwise biradical mechanism.
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spelling pubmed-54770382017-06-28 Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene Guo, Jing Liu, Yangbin Li, Xiangqiang Liu, Xiaohua Lin, Lili Feng, Xiaoming Chem Sci Chemistry A chiral Lewis acid-promoted enantioselective cyclopropanation using phenyliodonium ylide as the carbene precursor was developed. A variety of spirocyclopropane-oxindoles with contiguous tertiary and all carbon quaternary centers were obtained in excellent outcomes (up to 99% yield, >19 : 1 d.r., up to 99% ee). EPR spectroscopy study supported a stepwise biradical mechanism. Royal Society of Chemistry 2016-04-01 2016-01-04 /pmc/articles/PMC5477038/ /pubmed/28660046 http://dx.doi.org/10.1039/c5sc03658e Text en This journal is © The Royal Society of Chemistry 2016 https://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
Guo, Jing
Liu, Yangbin
Li, Xiangqiang
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
title Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
title_full Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
title_fullStr Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
title_full_unstemmed Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
title_short Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
title_sort nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5477038/
https://www.ncbi.nlm.nih.gov/pubmed/28660046
http://dx.doi.org/10.1039/c5sc03658e
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