Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols

[Image: see text] The silyl-Prins cyclization of geminal vinylsilyl alcohols and aldehydes, promoted by TMSOTf, provides access to polysubstituted tetrahydropyrans in which the silyl group remains in the molecule and an aryl group has migrated from silicon to carbon. This domino silyl-Prins/aryl mig...

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Autores principales: Díez-Poza, Carlos, Barbero, Asunción
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576834/
https://www.ncbi.nlm.nih.gov/pubmed/34615353
http://dx.doi.org/10.1021/acs.orglett.1c03121
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author Díez-Poza, Carlos
Barbero, Asunción
author_facet Díez-Poza, Carlos
Barbero, Asunción
author_sort Díez-Poza, Carlos
collection PubMed
description [Image: see text] The silyl-Prins cyclization of geminal vinylsilyl alcohols and aldehydes, promoted by TMSOTf, provides access to polysubstituted tetrahydropyrans in which the silyl group remains in the molecule and an aryl group has migrated from silicon to carbon. This domino silyl-Prins/aryl migration process is general and high-yielding for aryl, vinyl, or alkyl aldehydes. Moreover, cyclization proceeds with very high stereocontrol in a one-pot reaction in which both quaternary and tertiary stereogenic centers have been created.
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spelling pubmed-85768342021-11-10 Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols Díez-Poza, Carlos Barbero, Asunción Org Lett [Image: see text] The silyl-Prins cyclization of geminal vinylsilyl alcohols and aldehydes, promoted by TMSOTf, provides access to polysubstituted tetrahydropyrans in which the silyl group remains in the molecule and an aryl group has migrated from silicon to carbon. This domino silyl-Prins/aryl migration process is general and high-yielding for aryl, vinyl, or alkyl aldehydes. Moreover, cyclization proceeds with very high stereocontrol in a one-pot reaction in which both quaternary and tertiary stereogenic centers have been created. American Chemical Society 2021-10-07 2021-11-05 /pmc/articles/PMC8576834/ /pubmed/34615353 http://dx.doi.org/10.1021/acs.orglett.1c03121 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Díez-Poza, Carlos
Barbero, Asunción
Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols
title Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols
title_full Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols
title_fullStr Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols
title_full_unstemmed Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols
title_short Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols
title_sort unexpected domino silyl-prins/aryl migration process from geminal vinylsilyl alcohols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576834/
https://www.ncbi.nlm.nih.gov/pubmed/34615353
http://dx.doi.org/10.1021/acs.orglett.1c03121
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