Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes

Academic Article
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related to degree

  • Halvorsen, Geoff, Ph.D. in Chemistry, Scripps Research , Transferred from University of Michigan 2005 - 2012

publication date

  • May 2007

abstract

  • The synthesis of siloxacyclopentene-constrained trienes 7 and 10 and studies of their IMDA cycloadditions are described. The use of appropriately chosen thermal or Lewis acid conditions allows for cycloadducts 3-6 to be obtained with high levels of diastereoselectivity. These adducts possess trans-relationships between the hydroxyl group and the adjacent ring fusion proton, a stereochemical relationship not previously attainable in IMDA reactions.