Cyclopropenium-activated cyclodehydration of diols.
The dehydrative cyclization of diols to cyclic ethers via cyclopropenium activation is described. Using 2,3-diphenylcyclopropene and methanesulfonic anhydride, a series of 1,4- and 1,5-diols are rapidly cyclized to furnish tetrahydrofurans and tetrahydropyrans in high yield. Eleven total substrates are shown, including a gram scale cyclization of a diterpene derivative.
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Brendan D
BD
Kelly
Tristan H
TH
Lambert