Enzymatic desymmetrization of meso-2,3-bis(acetoxymethyl) and bis(hydroxymethyl) substituted hexachloronorbornadiene derivatives

Tanyeli C., KARADAĞ T., AKHMEDOV İ. M.

TETRAHEDRON-ASYMMETRY, vol.15, no.2, pp.307-310, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 2
  • Publication Date: 2004
  • Doi Number: 10.1016/j.tetasy.2003.11.023
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.307-310
  • Middle East Technical University Affiliated: Yes

Abstract

meso-Bis(acetoxymethyl)-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hepta-2,5-diene and i)ieso-bis(hydroxymethyl)-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hepta-2,5-diene were transformed into chiral monoesters with 65-92% ee via enzymatic desymmetrization using various lipases. The absolute configuration was determined by transforming 2-acetoxymethyl-3-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hepta-2,5-diene into the 2-acetoxymethyl-3-hydi-oxymethylbicyclo[2.2.1]hepta-2,5-diene of known absolute configuration. (C) 2003 Elsevier Ltd. All rights reserved.