Tetrahedron

Use of temporary tethers in the intramolecular [2+ 2] photocycloaddition reactions of tetrahydrophthalimide derivatives: a new approach to complex tricyclic lactones

Ş Gülten, A Sharpe, JR Baker, KI Booker-Milburn

Index: Guelten, Sirin; Sharpe, Andrew; Baker, James R.; Booker-Milburn, Kevin I. Tetrahedron, 2007 , vol. 63, # 18 p. 3659 - 3671

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Citation Number: 7

Abstract

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. ...