Linker-Oriented Design of Binaphthol Derivatives for Optical Resolution Using Lipase-Catalyzed Reaction.

[摘要]：Candida antarctica lipase B (CAL-B), the one of the most frequently used enzymes in org. synthesis for the prepn. of optically active alcs., has not, however, been used before for the optical resoln. of (?-2,2'-binaphthols. Here, an efficient linker-oriented design of 2,2'-binaphthol derivs. that is appropriate for optical resoln. using CAL-B-catalyzed hydrolysis reaction has been established. Me 4-(1-(6-bromo-2-methoxymethoxynaphthalen-1-yl)-6-bromonaphthalen- 2-yloxy)butanoate was hydrolyzed by CAL-B to afford the corresponding acid with excellent enantioselectivity (E > 200). Two types of optically active binaphthol derivs., 1-(2-hydroxy-6-(naphthalen-1-yl)naphthalen-1-yl)-6-(naphthalen-1-yl)nap hthalen-2-ol and 6-butyl-1-(6-butyl-2-hydroxynaphthalen-1-yl)naphthalen-2-ol, were prepd. by this chemoenzymic reaction protocol and used as chiral templates for asym. addn. and Henry reactions.

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