Secondary alcohols act as better nucleophiles than primary alcohols in the lipase-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxyls

Tetrahedron Letters

Volumn 48, Issue 47, 2007, Pages 8334-8337

  Miyazawa, Toshifumi ^a   Hamada, Manabu ^a   Morimoto, Ryohei ^a   Murashima, Takashi ^a   Yamada, Takashi ^a  

^a KONAN UNIVERSITY   (Japan)

Author keywords

Candida antarctica lipase B; Hydroquinones; Regioselective deacylation; Resorcinols; Secondary alcohols

Indexed keywords

ALCOHOL DERIVATIVE; BENZENE DERIVATIVE; DIHYDROXYBENZENE DERIVATIVE; HYDROQUINONE; LIPASE B; PHENOL; RESORCINOL; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DEACYLATION; ENZYME MECHANISM; STEREOCHEMISTRY; SUBSTITUTION REACTION;

CANDIDA ANTARCTICA;

EID: 35348971409     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.104     Document Type: Article

References (17)

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11. 3), 6.92 (1H, d, J = 2.5 Hz, H-2), 6.98 (1H, dd, J = 8.5 and 2.5 Hz, H-6), 7.33 (1H, d, J = 8.5 Hz, H-5).
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13. 1H NMR (500 MHz) analysis for the quantification of the reaction products. The proton signals in the aromatic region were mainly employed for the purpose. The whole content of the reaction mixture was used up for one analysis, and several discrete reaction mixtures were used at different reaction times.
14. 3), 6.46 (1H, dd, J = 8.5 and 2.5 Hz, H-6), 6.52 (1H, d, J = 2.5 Hz, H-2), 7.05 (1H, d, J = 8.5 Hz, H-5), 9.55 (1H, s, OH).
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