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J Org Chem. 2013 Nov 15;78(22):11618-22. doi: 10.1021/jo402036u. Epub 2013 Nov 5.

H-bonding activation in highly regioselective acetylation of diols.

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1
School of Chemistry & Chemical Engineering, Huazhong University of Science & Technology , Luoyu Road 1037, Wuhan 430074, P. R. China.

Abstract

H-bonding activation in the regioselective acetylation of vicinal and 1,3-diols is presented. Herein, the acetylation of the hydroxyl group with acetic anhydride can be activated by the formation of H-bonds between the hydroxyl group and anions. The reaction exhibits high regioselectivity when a catalytic amount of tetrabutylammonium acetate is employed. Mechanistic studies indicated that acetate anion forms dual H-bonding complexes with the diol, which facilitates the subsequent regioselective monoacetylation.

PMID:
24164588
DOI:
10.1021/jo402036u

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