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

Şirin Gülten, Andrew Sharpe, James R. Baker, Kevin I. Booker-Milburn*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

5 Citations (Scopus)

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. 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. © 2007 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3659-3671
Number of pages13
JournalTetrahedron
Volume63
Issue number18
DOIs
Publication statusPublished - 30 Apr 2007

Bibliographical note

Publisher: Elsevier

Keywords

  • Acid-catalysed rearrangements
  • Cycloadditions
  • Photochemistry
  • Temporary tethers

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