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Org Lett. 2011 Feb 18;13(4):740-3. doi: 10.1021/ol102980t. Epub 2011 Jan 19.

Cyclopropenium-activated cyclodehydration of diols.

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  • 1Department of Chemistry, Columbia University, New York, New York 10027, USA.

Abstract

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.

PMID:
21247136
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