Acid-catalyzed Grob fragmentation reactions of acetonides derived from terpenes.
[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.
Barluenga
José
J
Instituto 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
Alvarez-Pérez
Mónica
M
Wuerth
Kirsten
K
Rodríguez
Félix
F
Fañanás
Francisco J
FJ