Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5228023 | Tetrahedron | 2007 | 13 Pages |
Abstract
The intramolecular [2+2] photocycloaddition reactions of a series of alkenols tethered to ethanolamine, l-(+)-valinol and R-(â)-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.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Åirin Gülten, Andrew Sharpe, James R. Baker, Kevin I. Booker-Milburn,