Organic letters

Silver (I) oxide mediated highly selective monotosylation of symmetrical diols. Application to the synthesis of polysubstituted cyclic ethers

A Bouzide, G Sauvé

Index: Bouzide, Abderrahim; Sauve, Gilles Organic Letters, 2002 , vol. 4, # 14 p. 2329 - 2332

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Citation Number: 123

Abstract

The reaction of symmetrical diols and oligo (ethylene glycol) s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver (I) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields. Polysubstituted cyclic ethers were obtained readily upon treatment of the corresponding diols with an excess of silver oxide. The high selectivity was explained on the basis of the ...