960602-01-1Relevant academic research and scientific papers
Secondary alcohols act as better nucleophiles than primary alcohols in the lipase-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxyls
Miyazawa, Toshifumi,Hamada, Manabu,Morimoto, Ryohei,Murashima, Takashi,Yamada, Takashi
, p. 8334 - 8337 (2007)
Candida antarctica lipase B (CAL-B) was found to be highly regioselective as well as active in the deacylation of resorcinols and hydroquinones acylated at both phenolic hydroxyls. Contrary to expectation, secondary alcohols acted as better nucleophiles than primary alcohols in these enzymatic deacylations.
Candida antarctica lipase B-mediated regioselective acylation of dihydroxybenzenes in organic solvents
Miyazawa, Toshifumi,Hamada, Manabu,Morimoto, Ryohei,Maeda, Yuki
, p. 3915 - 3923 (2015/06/02)
Candida antarctica lipase B proved to be a highly active biocatalyst for the direct acylation of phenolic hydroxy groups of substituted hydroquinones and resorcinols, which have rarely been reported so far. More importantly, the acylation reactions took place generally in a markedly regioselective manner: the hydroxy group remote from the substituent was preferentially acylated. In the case of substituted hydroquinones, the selectivity increased with the increase in the bulk of the substituent. Interestingly, the 1-O-monoacylated derivatives were obtained as the sole products in the case of 4-substituted resorcinols.
