Enzyme catalyzed reverse enantiomeric separation of methyl (+/-)-3-cyclohexene-1-carboxylate

Tanyeli C., Turkut E.

TETRAHEDRON-ASYMMETRY, vol.15, no.13, pp.2057-2060, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 13
  • Publication Date: 2004
  • Doi Number: 10.1016/j.tetasy.2004.05.034
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2057-2060
  • Middle East Technical University Affiliated: Yes

Abstract

We describe the differences of hydrolase-type enzymes pig liver esterase (PLE), horse liver esterase (HLE), and porcine pancreatic lipase (PPL) on the hydrolysis of methyl (+/-)-3-cyclohexene-1-carboxylate to afford both enantiomers with 89% to > 99% ee. The resultant enantiomerically pure (S)-(-)-3-cyclohexene-1-carboxylic acid was transformed into (1S,5S)-(-)-5-(hydroxymethyl)-2-cyclohexen-1-ol via iodolactonization, subsequent elimination of iodine with 1,8-diazibicyclo[5.4.0]undec-7-ene (DBU) and reduction with lithium aluminum hydride (LAH). (C) 2004 Elsevier Ltd. All rights reserved.