Cyclic enol ether synthesis via arenesulfonyl iodide additions to alkynols

GL Edwards, CA Muldoon, DJ Sinclair

Index: Edwards, Gavin L.; Muldoon, Craig A.; Sinclair, David J. Tetrahedron, 1996 , vol. 52, # 22 p. 7779 - 7788

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Citation Number: 34

Abstract

The reaction of arenesulfonyl iodides with alkynols generally provides adducts in good yields. Treatment of these adducts with KN (SiMe3) 2 gives enol ethers; cyclisation of the functionalised pentenol (5) results in formation of the exo-alkylidene tetrahydrofuran (7), whereas the homologous hexenol (6) gives the dihydropyran (8). Attempts to cyclise the hexenol (6) with potassium t-butoxide under the conditions reported by Short and Ziegler ...