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Pàgina inicial > Articles > Articles publicats > Intramolecular photocycloaddition of 2(5H)-furanones to temporarily tethered terminal alkenes as a stereoselective source of enantiomerically pure polyfunctionalyzed cyclobutanes |
Data: | 2018 |
Resum: | Allyloxymethyloxymethyl and 4-pentenoyloxymethyl substituents have been used as tethering groups to study the intramolecular [2 + 2] photocycloaddition of chiral 5-substituted 2(5H)-furanones. The photoreactions proceed in good yield and provide the expected regio- and diastereoselective tricyclic compounds with complementary regioselectivity, which depends on whether the vinyl chain is attached to the furanone by an acetal or an ester linkage. Computational simulations agree with experimental observations and indicate that the origin of the different observed regioselectivity in the intramolecular photochemical reaction of lactones 5 and 6 arises from the relative stability of the initial conformers. The synthetic potential of the enantiomerically pure photoadducts is illustrated by preparing an all-cis 1,2,3-trisubstituted cyclobutane bearing fully orthogonally protected hydroxyl groups. |
Ajuts: | Ministerio de Economía y Competitividad CTQ2016-75363-R Ministerio de Economía y Competitividad CTQ2014-59544-P Ministerio de Economía y Competitividad CTQ2013-41161-R Agència de Gestió d'Ajuts Universitaris i de Recerca 2014/SGR-482 |
Drets: | Tots els drets reservats. |
Llengua: | Anglès |
Document: | Article ; recerca ; Versió acceptada per publicar |
Matèria: | Irradiation ; Lactones ; Mixtures ; Molecular structure ; Solvents |
Publicat a: | Journal of organic chemistry, Vol. 83 Núm. 6 (2018) , p. 3188-3199, ISSN 1520-6904 |
Postprint 34 p, 1.0 MB |