Selective protection of 1, 2-and 1, 3-diols via acylative cleavage of cyclic formals

WF Bailey, LMJ Zarcone, AD Rivera

Index: Bailey, William F.; Zarcone, Lyn M. J.; Rivera, Alberto D. Journal of Organic Chemistry, 1995 , vol. <8> 60, p. 2532 - 2536

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Citation Number: 22

Abstract

An efficient two-step method for the differential functionalization of 1, 2-and 1, 3-diols, involving regioselective cleavage of five-and six-membered cyclic formals with acetyl chloride followed by conversion of the resulting chloromethyl ether acetate 1 to an alkoxymethyl ether acetate (21, has been developed. When applied to unsymmetrically substituted cyclic formals, the differential functionalization sequence is highly selective ...