Enzyme-catalyzed resolution of aromatic ring fused cyclic tertiary alcohols

Ozdemirhan D., Sezer S., Sonmez Y.

TETRAHEDRON-ASYMMETRY, vol.19, no.23, pp.2717-2720, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 19 Issue: 23
  • Publication Date: 2008
  • Doi Number: 10.1016/j.tetasy.2008.12.002
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2717-2720
  • Middle East Technical University Affiliated: Yes

Abstract

An efficient chemoenzymatic route for the synthesis of optically active aromatic ring fused cyclic tertiary alcohols (S)-(-)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol (-)-1b and (S)-(+)-1-methyl-2,3-dihydro-1H-inden-1-ol (+)-1a has been developed. Different lipases have been tested in the transesterification of these tertiary alcohols; CAL-A (Candida antarctica Lipase A) was found to be the best biocatalyst for 1b and CAL-A-CLEA (Lipase A, C. antarctica, cross-linked enzyme aggregate) for la, obtained with ee values of 20% and 45%, respectively, and the corresponding esters 2b and 2a with the ee values of 99% and 71%, respectively. (C) 2008 Elsevier Ltd. All rights reserved.