Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization

Scoccia, Jimena; Pérez, Sixto J.; Sinka, Victoria; Cruz, Daniel A.; López-Soria, Juan M.; Fernández, Israel; Martín, Víctor S.; Miranda, Pedro O.; Padrón, Juan I.; European Commission

Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization

A new, direct, and diastereoselective synthesis of activated 2,3,4,6-tetrasubstituted tetrahydro-2H-pyrans is described. In this reaction, iron(III) catalyzed an SN2′–Prins cyclization tandem process leading to the creation of three new stereocenters in one single step. These activated tetrahydro-2H-pyran units are easily derivatizable through CuAAC conjugations in order to generate multifunctionalized complex molecules. DFT calculations support the in situ SN2′ reaction as a preliminary step in the Prins cyclization.

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Bibliographic Details
Main Authors:	Scoccia, Jimena, Pérez, Sixto J., Sinka, Victoria, Cruz, Daniel A., López-Soria, Juan M., Fernández, Israel, Martín, Víctor S., Miranda, Pedro O., Padrón, Juan I.
Other Authors:	European Commission
Format:	artículo biblioteca
Published:	American Chemical Society 2017-08-31
Online Access:	http://hdl.handle.net/10261/184912 http://dx.doi.org/10.13039/501100007757 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329
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spelling	dig-ipna-es-10261-1849122019-11-14T09:22:23Z Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization Scoccia, Jimena Pérez, Sixto J. Sinka, Victoria Cruz, Daniel A. López-Soria, Juan M. Fernández, Israel Martín, Víctor S. Miranda, Pedro O. Padrón, Juan I. European Commission Agencia Canaria de Investigación, Innovación y Sociedad de la Información Ministerio de Economía y Competitividad (España) A new, direct, and diastereoselective synthesis of activated 2,3,4,6-tetrasubstituted tetrahydro-2H-pyrans is described. In this reaction, iron(III) catalyzed an SN2′–Prins cyclization tandem process leading to the creation of three new stereocenters in one single step. These activated tetrahydro-2H-pyran units are easily derivatizable through CuAAC conjugations in order to generate multifunctionalized complex molecules. DFT calculations support the in situ SN2′ reaction as a preliminary step in the Prins cyclization. This research was supported by the Spanish MINECO, co-financed by the European Regional Development Fund (ERDF) (CTQ2014- 56362-C2-1-P) and MINECO-FEDER (CTQ2016-78205-P and CTQ2014-51912-REDC to I. F). D. A. C thanks the Spanish MINECO for an F.P.I fellowship. J. M. L-S thanks the Canary Island Government (ACIISI) for a pre-doctoral contract. P. O. M was supported by a Marie Curie IOF from the European Union’s Seventh Framework Program FP7/2007-2013 under REA Grant Agreement No. 623155. Peer Reviewed 2019-06-26T12:18:47Z 2019-06-26T12:18:47Z 2017-08-31 2019-06-26T12:18:48Z artículo http://purl.org/coar/resource_type/c_6501 Organic Letters 19(18): 4834-4837 (2017) 1523-7060 http://hdl.handle.net/10261/184912 10.1021/acs.orglett.7b02270 1523-7052 http://dx.doi.org/10.13039/501100007757 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-56362-C2-1-P info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-78205-P info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-51912 info:eu-repo/grantAgreement/EC/FP7/623155 Postprint https://doi.org/10.1021/acs.orglett.7b02270 Sí open American Chemical Society
institution	IPNA ES
collection	DSpace
country	España
countrycode	ES
component	Bibliográfico
access	En linea
databasecode	dig-ipna-es
tag	biblioteca
region	Europa del Sur
libraryname	Biblioteca del IPNA España
description	A new, direct, and diastereoselective synthesis of activated 2,3,4,6-tetrasubstituted tetrahydro-2H-pyrans is described. In this reaction, iron(III) catalyzed an SN2′–Prins cyclization tandem process leading to the creation of three new stereocenters in one single step. These activated tetrahydro-2H-pyran units are easily derivatizable through CuAAC conjugations in order to generate multifunctionalized complex molecules. DFT calculations support the in situ SN2′ reaction as a preliminary step in the Prins cyclization.
author2	European Commission
author_facet	European Commission Scoccia, Jimena Pérez, Sixto J. Sinka, Victoria Cruz, Daniel A. López-Soria, Juan M. Fernández, Israel Martín, Víctor S. Miranda, Pedro O. Padrón, Juan I.
format	artículo
author	Scoccia, Jimena Pérez, Sixto J. Sinka, Victoria Cruz, Daniel A. López-Soria, Juan M. Fernández, Israel Martín, Víctor S. Miranda, Pedro O. Padrón, Juan I.
spellingShingle	Scoccia, Jimena Pérez, Sixto J. Sinka, Victoria Cruz, Daniel A. López-Soria, Juan M. Fernández, Israel Martín, Víctor S. Miranda, Pedro O. Padrón, Juan I. Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization
author_sort	Scoccia, Jimena
title	Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization
title_short	Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization
title_full	Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization
title_fullStr	Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization
title_full_unstemmed	Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization
title_sort	direct access to 2,3,4,6-tetrasubstituted tetrahydro-2h-pyrans via tandem sn2′–prins cyclization
publisher	American Chemical Society
publishDate	2017-08-31
url	http://hdl.handle.net/10261/184912 http://dx.doi.org/10.13039/501100007757 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329
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Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization

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