INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL-TETHERED TRIENES

P J AINSWORTH, D CRAIG, J C READER, A M Z SLAWIN, A J P WHITE, D J WILLIAMS

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

The synthesis and intramolecular Diels-Alder reactions of a series of silyl acetal-tethered trienes 4-9 are described. The cycloadditions show complete regioselectivity, and in all but one case give exclusively cis-fused bicyclic products. The selectivities are rationalised in terms of stereoelectronic and steric effects.

Original languageEnglish
Pages (from-to)11601-11622
Number of pages22
JournalTetrahedron
Volume51
Issue number42
Publication statusPublished - 16 Oct 1995

Keywords

  • POLAR TRANSITION-STATE
  • CYCLO-ADDITIONS
  • CYCLOADDITIONS
  • DIENOPHILE
  • 1,2,4-TRIAZINES
  • SUBSTITUENTS
  • SELECTIVITY
  • PYRIDINES
  • DIENES
  • ETHER

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