Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols

By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols was achieved using NIS as a halogen source. Based on this reaction, one-pot asymmetric 3-exo iodo-cycloethe...

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Autores principales: Shen, Zhigao, Pan, Xixian, Lai, Yisheng, Hu, Jiadong, Wan, Xiaolong, Li, Xiaoge, Zhang, Hui, Xie, Weiqing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5947518/
https://www.ncbi.nlm.nih.gov/pubmed/29861937
http://dx.doi.org/10.1039/c5sc02485d
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author Shen, Zhigao
Pan, Xixian
Lai, Yisheng
Hu, Jiadong
Wan, Xiaolong
Li, Xiaoge
Zhang, Hui
Xie, Weiqing
author_facet Shen, Zhigao
Pan, Xixian
Lai, Yisheng
Hu, Jiadong
Wan, Xiaolong
Li, Xiaoge
Zhang, Hui
Xie, Weiqing
author_sort Shen, Zhigao
collection PubMed
description By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols was achieved using NIS as a halogen source. Based on this reaction, one-pot asymmetric 3-exo iodo-cycloetherification/Wagner–Meerwein rearrangement of allyl alcohols en route to enantioenriched 2-iodomethyl-2-aryl cycloalkanones was subsequently developed. Due to the participation of adjacent iodine, the Wagner–Meerwein rearrangement of 2-iodomethyl-2-aryl epoxide proceeds with unusual retention of stereoconfiguration.
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spelling pubmed-59475182018-06-01 Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols Shen, Zhigao Pan, Xixian Lai, Yisheng Hu, Jiadong Wan, Xiaolong Li, Xiaoge Zhang, Hui Xie, Weiqing Chem Sci Chemistry By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols was achieved using NIS as a halogen source. Based on this reaction, one-pot asymmetric 3-exo iodo-cycloetherification/Wagner–Meerwein rearrangement of allyl alcohols en route to enantioenriched 2-iodomethyl-2-aryl cycloalkanones was subsequently developed. Due to the participation of adjacent iodine, the Wagner–Meerwein rearrangement of 2-iodomethyl-2-aryl epoxide proceeds with unusual retention of stereoconfiguration. Royal Society of Chemistry 2015-12-01 2015-08-27 /pmc/articles/PMC5947518/ /pubmed/29861937 http://dx.doi.org/10.1039/c5sc02485d Text en This journal is © The Royal Society of Chemistry 2015 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
Shen, Zhigao
Pan, Xixian
Lai, Yisheng
Hu, Jiadong
Wan, Xiaolong
Li, Xiaoge
Zhang, Hui
Xie, Weiqing
Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
title Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
title_full Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
title_fullStr Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
title_full_unstemmed Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
title_short Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
title_sort chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5947518/
https://www.ncbi.nlm.nih.gov/pubmed/29861937
http://dx.doi.org/10.1039/c5sc02485d
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