A telluride-triggered nucleophilic ring opening of monoactivated cyclopropanes.
[reaction: see text] Acylcyclopropanemethanol tosylates undergo rapid ring opening at room temperature by the action of lithium telluride to produce the enolate of a homoallylic ketone. The enolate can be protonated to yield the corresponding ketone or treated with benzaldehyde to give the aldol product with good syn or anti diastereoselectivity depending on the conditions.
Avilov
Dmitry V
DV
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA.
Malusare
Mahesh G
MG
Arslancan
Engin
E
Dittmer
Donald C
DC