2026-04-17T12:06:34Zhttps://recercat.cat/oai/request

oai:recercat.cat:2072/4689292026-03-28T08:47:12Zcom_2072_98col_2072_378192

00925njm 22002777a 4500 dc Xin, Yangchun author Rodríguez Santiago, Luis author Sodupe Roure, Mariona author Álvarez-Fernández, Alejandra author Busqué Sánchez, Félix author Alibes, Ramón author 2018 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. Irradiation Lactones Mixtures Molecular structure Solvents Intramolecular photocycloaddition of 2(5H)-furanones to temporarily tethered terminal alkenes as a stereoselective source of enantiomerically pure polyfunctionalyzed cyclobutanes