886206-66-2Relevant academic research and scientific papers
H-bonding activation in highly regioselective acetylation of diols
Zhou, Yixuan,Rahm, Martin,Wu, Bin,Zhang, Xiaoling,Ren, Bo,Dong, Hai
, p. 11618 - 11622 (2013/12/04)
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.
Stereoelectronic control in regioselective carbohydrate protection
Dong, Hai,Zhou, Yixuan,Pan, Xiaoliang,Cui, Fengchao,Liu, Wei,Liu, Jingyao,Ramstroem, Olof
, p. 1457 - 1467 (2012/04/04)
Organotin-mediated regioselective protection has been extensively used in organic synthesis for many years. However, the mechanistic origin of the resulting regioselectivity is still not clear. By the comparison of the steric and stereoelectronic effects
Stereospecific ester activation in nitrite-mediated carbohydrate epimerization
Dong, Hai,Pei, Zhichao,Ramstroem, Olof
, p. 3306 - 3309 (2007/10/03)
The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In the present study, epimerization of gluco- and galactopyranoside derivatives to the corresponding
