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    Use of temporary tethers in the intramolecular [2+2] photocycloaddition reactions of tetrahydrophthalimide derivatives
    (Pergamon-Elsevier Science Ltd, 2007) Gulten, Sirin; Sharpe, Andrew; Baker, James R.; Booker-Milburn, Kevin I.
    The intramolecular [2+2] photocycloaddition reactions of a series of alkenols tethered to ethanolamine, L-(+)-valinol and R-(-)-2-phenylglycinol derived 3,4,5,6-tetrahydrophthalimides via a carbonate or silicon linkage have been examined. These [2+2] photocycloadditions gave the corresponding cyclobutanes in high yield with complete endo control in all cases and with diastereoselectivities as high as 8:1 with the chiral tethers. The cleavage of the temporary tethers by either desilylation or hydrolysis provided the endo diols. Cleavage of the ethanolamine linkage by reduction/hydrolysis precipitated an acid-catalysed fragmentation/ring expansion sequence to generate complex tricyclic lactones. (C) 2007 Elsevier Ltd. All rights reserved.