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Silyl Enol Ether Prins Cyclization: Diastereoselective Formation of Substituted Tetrahydropyran-4-ones
[Image: see text] A diastereoselective synthesis of cis-2,6-disubstituted tetrahydropyran-4-ones was developed. The key step of this methodology, a silyl enol ether Prins cyclization, was promoted by a condensation reaction between a hydroxy silyl enol ether and an aldehyde to afford substituted tet...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168786/ https://www.ncbi.nlm.nih.gov/pubmed/25200563 http://dx.doi.org/10.1021/jo501580p |
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author | Tay, Gidget C. Huang, Chloe Y. Rychnovsky, Scott D. |
author_facet | Tay, Gidget C. Huang, Chloe Y. Rychnovsky, Scott D. |
author_sort | Tay, Gidget C. |
collection | PubMed |
description | [Image: see text] A diastereoselective synthesis of cis-2,6-disubstituted tetrahydropyran-4-ones was developed. The key step of this methodology, a silyl enol ether Prins cyclization, was promoted by a condensation reaction between a hydroxy silyl enol ether and an aldehyde to afford substituted tetrahydropyran-4-ones. The cyclization was tolerant of many functional groups, and the modular synthesis of the hydroxy silyl enol ether allowed for the formation of more than 30 new tetrahydropyran-4-ones with up to 97% yield and >95:5 dr. The cyclization step forms new carbon–carbon and carbon–oxygen bonds, as well as a quaternary center with good diastereoselectivity. The method provides a versatile route for the synthesis of substituted tetrahydropyrans. |
format | Online Article Text |
id | pubmed-4168786 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-41687862015-09-09 Silyl Enol Ether Prins Cyclization: Diastereoselective Formation of Substituted Tetrahydropyran-4-ones Tay, Gidget C. Huang, Chloe Y. Rychnovsky, Scott D. J Org Chem [Image: see text] A diastereoselective synthesis of cis-2,6-disubstituted tetrahydropyran-4-ones was developed. The key step of this methodology, a silyl enol ether Prins cyclization, was promoted by a condensation reaction between a hydroxy silyl enol ether and an aldehyde to afford substituted tetrahydropyran-4-ones. The cyclization was tolerant of many functional groups, and the modular synthesis of the hydroxy silyl enol ether allowed for the formation of more than 30 new tetrahydropyran-4-ones with up to 97% yield and >95:5 dr. The cyclization step forms new carbon–carbon and carbon–oxygen bonds, as well as a quaternary center with good diastereoselectivity. The method provides a versatile route for the synthesis of substituted tetrahydropyrans. American Chemical Society 2014-09-09 2014-09-19 /pmc/articles/PMC4168786/ /pubmed/25200563 http://dx.doi.org/10.1021/jo501580p Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | Tay, Gidget C. Huang, Chloe Y. Rychnovsky, Scott D. Silyl Enol Ether Prins Cyclization: Diastereoselective Formation of Substituted Tetrahydropyran-4-ones |
title | Silyl Enol Ether Prins Cyclization:
Diastereoselective
Formation of Substituted Tetrahydropyran-4-ones |
title_full | Silyl Enol Ether Prins Cyclization:
Diastereoselective
Formation of Substituted Tetrahydropyran-4-ones |
title_fullStr | Silyl Enol Ether Prins Cyclization:
Diastereoselective
Formation of Substituted Tetrahydropyran-4-ones |
title_full_unstemmed | Silyl Enol Ether Prins Cyclization:
Diastereoselective
Formation of Substituted Tetrahydropyran-4-ones |
title_short | Silyl Enol Ether Prins Cyclization:
Diastereoselective
Formation of Substituted Tetrahydropyran-4-ones |
title_sort | silyl enol ether prins cyclization:
diastereoselective
formation of substituted tetrahydropyran-4-ones |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168786/ https://www.ncbi.nlm.nih.gov/pubmed/25200563 http://dx.doi.org/10.1021/jo501580p |
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