jo8b00088_si_003.cif (114.06 kB)
Intramolecular Photocycloaddition of 2(5H)‑Furanones to Temporarily Tethered Terminal Alkenes as a Stereoselective Source of Enantiomerically Pure Polyfunctionalyzed Cyclobutanes
dataset
posted on 2018-02-20, 00:00 authored by Yangchun Xin, Luís Rodríguez-Santiago, Mariona Sodupe, Angel Álvarez-Larena, Félix Busqué, Ramon AlibésAllyloxymethyloxymethyl
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.
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originfuranoneTemporarily Tethered Terminal Alkenesintramolecularester linkageregioselectivityphotoadductcicyclobutanechiral 5-conformerstabilityvinyl chainacetalphotocycloadditionEnantiomerically Pure Polyfunctionalyzed Cyclobutanes Allyloxymethyloxymethylhydroxyl groupsregioorthogonallyenantiomericallytrisubstitutedtethering groupsStereoselective Sourcelactones 5FuranoneIntramolecular Photocycloadditionphotoreaction4- pentenoyloxymethyl substituentsComputational simulationsdiastereoselective tricyclic compounds
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