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Acid-catalyzed Grob fragmentation reactions of acetonides derived from terpenes
José Barluenga1, Mónica Alvarez-Pérez, Kirsten Wuerth
1Instituto Universitario de Química Organometálica "Enrique Moles", Unidad Asociada al C.S.I.C. Julián Clavería, 8, Universidad de Oviedo, 33006-Oviedo, Spain. barluenga@sauron.quimica.uniovi.es
Organic Letters
|March 14, 2003
Abstract:
[reaction: see text] Acetonides derived from different terpenes undergo Grob fragmentation by treatment with a catalytic amount of acid, triflic acid, or boron trifluoride, giving aldehydes containing a cyclopropane or cyclobutane ring with good yields and complete diastereoselectivity. The structure and the stereochemistry of the starting acetonide have a crucial influence on the reaction course.