H-Bonding Activation in Highly Regioselective Acetylation of Diols.
Artikel i vetenskaplig tidskrift, 2013

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 amt. 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. [on SciFinder(R)]

regioselective acetylation

carbohydrates

hydrogen bonding activation

Density functional theory

Författare

Yixuan Zhou

Bin Wu

Xiaoling Zhang

Bo Ren

Hai. Dong

Journal of Organic Chemistry

0022-3263 (ISSN) 1520-6904 (eISSN)

Vol. 78 22 11618-11622

Ämneskategorier

Teoretisk kemi

Organisk kemi

DOI

10.1021/jo402036u