Linker-oriented design of binaphthol derivatives for optical resolution using lipase-catalyzed reaction

J Org Chem. 2008 May 16;73(10):3875-84. doi: 10.1021/jo800351h. Epub 2008 Apr 22.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Fungal Proteins
  • Hydrolysis
  • Lanthanum / chemistry
  • Lipase / chemistry*
  • Lithium / chemistry
  • Models, Molecular
  • Molecular Structure
  • Naphthols / chemical synthesis*
  • Naphthols / chemistry
  • Organometallic Compounds / chemistry
  • Stereoisomerism
  • Titanium / chemistry

Substances

  • Fungal Proteins
  • Naphthols
  • Organometallic Compounds
  • Lanthanum
  • Lithium
  • Titanium
  • Lipase
  • lipase B, Candida antarctica