Xin, Yangchun Rodríguez-Santiago, Luís Sodupe, Mariona Álvarez-Larena, Angel Busqué, Félix Alibés, Ramon Intramolecular Photocycloaddition of 2(5<i>H</i>)‑Furanones to Temporarily Tethered Terminal Alkenes as a Stereoselective Source of Enantiomerically Pure Polyfunctionalyzed Cyclobutanes Allyloxymethyloxymethyl and 4-pentenoyloxymethyl substituents have been used as tethering groups to study the intramolecular [2 + 2] photocycloaddition of chiral 5-substituted 2­(5<i>H</i>)-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 <b>5</b> and <b>6</b> arises from the relative stability of the initial conformers. The synthetic potential of the enantiomerically pure photoadducts is illustrated by preparing an all-<i>cis</i> 1,2,3-trisubstituted cyclobutane bearing fully orthogonally protected hydroxyl groups. origin;furanone;Temporarily Tethered Terminal Alkenes;intramolecular;ester linkage;regioselectivity;photoadduct;ci;cyclobutane;chiral 5-;conformer;stability;vinyl chain;acetal;photocycloaddition;Enantiomerically Pure Polyfunctionalyzed Cyclobutanes Allyloxymethyloxymethyl;hydroxyl groups;regio;orthogonally;enantiomerically;trisubstituted;tethering groups;Stereoselective Source;lactones 5;Furanone;Intramolecular Photocycloaddition;photoreaction;4- pentenoyloxymethyl substituents;Computational simulations;diastereoselective tricyclic compounds 2018-02-20
    https://acs.figshare.com/articles/dataset/Intramolecular_Photocycloaddition_of_2_5_i_H_i_Furanones_to_Temporarily_Tethered_Terminal_Alkenes_as_a_Stereoselective_Source_of_Enantiomerically_Pure_Polyfunctionalyzed_Cyclobutanes/5938693
10.1021/acs.joc.8b00088.s003