title: Linker-oriented design of binaphthol derivatives for optical resolution using lipase-catalyzed reaction.
abstract: Candida antarctica lipase B (CAL-B) is one the most frequently used enzymes in organic synthesis for the preparation of optically active alcohols. However, it has not been used for the optical resolution of (+/-)-2,2'-binaphthol. We established an efficient linker-oriented design of 2,2'-binaphthol derivatives that is appropriate for optical resolution using CAL-B-catalyzed hydrolysis reaction. Methyl 4-(1-(6-bromo-2-methoxymethoxynaphthalen-1-yl)-6-bromonaphthalen-2-yloxy)butanoate was hydrolyzed by CAL-B to afford a corresponding acid with excellent enantioselectivity ( E > 200). Two types of optically active binaphthol derivatives, 1-(2-hydroxy-6-(naphthalen-1-yl)naphthalen-1-yl)-6-(naphthalen-1-yl)naphthalen-2-ol and 6-butyl-1-(6-butyl-2-hydroxynaphthalen-1-yl)naphthalen-2-ol, were prepared by this chemo-enzymatic reaction protocol and were used as chiral templates for symmetric reactions.
authors.affiliation: Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Tottori, Japan.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Taniguchi
authors.forename: Taka-aki
authors.initials: TA
authors.lastname: Fukuba
authors.forename: Shuhei
authors.initials: S
authors.lastname: Nakatsuka
authors.forename: Shuichi
authors.initials: S
authors.lastname: Hayase
authors.forename: Motoi
authors.initials: M
authors.lastname: Kawatsura
authors.forename: Hidemitsu
authors.initials: H
authors.lastname: Uno
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Itoh
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D005656:Fungal Proteins; D006868:Hydrolysis; D007811:Lanthanum / Q000737:chemistry; D008049:Lipase / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
chemical_list: D005656:Fungal Proteins; D009284:Naphthols; D009942:Organometallic Compounds; D007811:Lanthanum; D008094:Lithium; D014025:Titanium; D008049:Lipase; C431349:lipase B, Candida antarctica