Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)

A series of optically active hypervalent iodine(III) reagents prepared from the corresponding (R)-2-(2-iodophenoxy)propanoate derivative was employed for the asymmetric dioxytosylation of styrene and its derivatives. The electrophilic addition of the hypervalent iodine(III) compound toward styrene p...

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Detalles Bibliográficos
Autores principales: Fujita, Morifumi, Miura, Koki, Sugimura, Takashi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870148/
https://www.ncbi.nlm.nih.gov/pubmed/29623128
http://dx.doi.org/10.3762/bjoc.14.53
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author Fujita, Morifumi
Miura, Koki
Sugimura, Takashi
author_facet Fujita, Morifumi
Miura, Koki
Sugimura, Takashi
author_sort Fujita, Morifumi
collection PubMed
description A series of optically active hypervalent iodine(III) reagents prepared from the corresponding (R)-2-(2-iodophenoxy)propanoate derivative was employed for the asymmetric dioxytosylation of styrene and its derivatives. The electrophilic addition of the hypervalent iodine(III) compound toward styrene proceeded with high enantioface selectivity to give 1-aryl-1,2-di(tosyloxy)ethane with an enantiomeric excess of 70–96% of the (S)-isomer.
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spelling pubmed-58701482018-04-05 Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III) Fujita, Morifumi Miura, Koki Sugimura, Takashi Beilstein J Org Chem Letter A series of optically active hypervalent iodine(III) reagents prepared from the corresponding (R)-2-(2-iodophenoxy)propanoate derivative was employed for the asymmetric dioxytosylation of styrene and its derivatives. The electrophilic addition of the hypervalent iodine(III) compound toward styrene proceeded with high enantioface selectivity to give 1-aryl-1,2-di(tosyloxy)ethane with an enantiomeric excess of 70–96% of the (S)-isomer. Beilstein-Institut 2018-03-20 /pmc/articles/PMC5870148/ /pubmed/29623128 http://dx.doi.org/10.3762/bjoc.14.53 Text en Copyright © 2018, Fujita et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Fujita, Morifumi
Miura, Koki
Sugimura, Takashi
Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)
title Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)
title_full Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)
title_fullStr Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)
title_full_unstemmed Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)
title_short Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)
title_sort enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(iii)
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870148/
https://www.ncbi.nlm.nih.gov/pubmed/29623128
http://dx.doi.org/10.3762/bjoc.14.53
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AT sugimuratakashi enantioselectivedioxytosylationofstyrenesusinglactatebasedchiralhypervalentiodineiii

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