Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes.
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.
Halvorsen
Geoff T
GT
Department of Chemistry and Biochemistry, Scripps-Florida, Jupiter, Florida 33458, USA.
Roush
William R
WR
D003517:Cyclopentanes / Q000737:chemistry*; D015394:Molecular Structure; D012833:Siloxanes / Q000737:chemistry*
D003517:Cyclopentanes; D012833:Siloxanes; C521219:siloxacyclopentene