Regiodivergent Electrophilic Cyclizations of Alkynylcyclobutanes for the Synthesis of Cyclobutane-Fused O-Heterocycles
Authors
Garre Hernández, María Soledad; Sucunza Sáenz, David; Aguilar, Enrique; García García, Patricia; Vaquero López, Juan J.Identifiers
Permanent link (URI): http://hdl.handle.net/10017/43792DOI: 10.1021/acs.joc.9b00618
ISSN: 0022-3263
Date
2019-05-03Bibliographic citation
The Journal of Organic Chemistry, 2019, v. 84, n. 9, p. 5712-5725
Keywords
Cyclobutane
dihydropyran
methylenetetrahydrofuran
gold
iodine
electrophilic cyclization
Project
CTQ2017-85263-R (Ministerio de Economía y Competitividad, AEI, FEDER); RETIC REDINREN RD16/0009/0015 (Instituto de Salud Carlos III, FEDER); CCG2015/EXP-003 (University of Alcalá)
info:eu-repo/grantAgreement/MINECO//CTQ2014-58688-R/ES/DESARROLLO DE UNA HERRAMIENTA HIPERESPECTRAL FORENSE PARA UN ANALISIS COMPLETO DE RESIDUOS DE DISPARO EN LA DIANA
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
© 2019 American Chemical Society
Access rights
info:eu-repo/semantics/openAccess
Abstract
Cyclobutane-fused dihydropyrans and methylenetetrahydrofurans are highly interesting cores found in numerous natural products. Both these cores are selectively prepared from a common alkynylcyclobutane precursor bearing an appended hydroxyl group herein. Thus, cyclobutane-fused dihydropyrans can be obtained by a selective 6-endo-dig iodocyclization, whereas gold-catalyzed 5-exo-dig cycloisomerization provides a bicyclic core containing a methylenetetrahydrofuran moiety as major product. Several cyclobutane-fused O-heterocycles with diverse substituents are synthesized following the reported methodology
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