Linker-oriented design of binaphthol derivatives for optical resolution using lipase-catalyzed reaction.
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.
Taniguchi
Tomohiro
T
Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Tottori, Japan.
Fukuba
Taka-aki
TA
Nakatsuka
Shuhei
S
Hayase
Shuichi
S
Kawatsura
Motoi
M
Uno
Hidemitsu
H
Itoh
Toshiyuki
T
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
D005656:Fungal Proteins; D009284:Naphthols; D009942:Organometallic Compounds; D007811:Lanthanum; D008094:Lithium; D014025:Titanium; D008049:Lipase; C431349:lipase B, Candida antarctica