ASYMMETRIC SYNTHESIS OF SOME CHIRAL ARYL AND HETERO ARYL-SUBSTITUTED beta-, gamma-, delta-HYDROXY ESTERS

Hasdemir B.

SYNTHETIC COMMUNICATIONS, vol.45, no.9, pp.1082-1088, 2015 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 45 Issue: 9
  • Publication Date: 2015
  • Doi Number: 10.1080/00397911.2014.1003353
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1082-1088
  • Keywords: Asymmetric synthesis, bioactive compounds, chiral hydroxy ester, enantiomeric excess, ENANTIOSELECTIVE SYNTHESIS, CHEMOENZYMATIC SYNTHESIS, KETO-ESTERS, REDUCTION, ACID, (R)-FLUOXETINE, ENANTIOMERS, INHIBITORS, LACTAM, CELLS
  • Istanbul University-Cerrahpasa Affiliated: No

Abstract

Sixteen chiral -, -, and -hydroxy esters with aryl, substituted aryl, and heteroaryl groups 2a-2s were synthesized by the asymmetric reduction of their corresponding keto esters 1a-1s as chiral pure reference compounds and starting materials. The asymmetric reduction was achieved by (R)-Me-CBS-oxazaborolidine. Ten new chiral - and -hydroxy esters 2d, 2e, and 2j-2s were obtained with high ee values and characterized by infrared, NMR (H-1 and C-13), mass spectrometry, chiral high-performance liquid chromatography, and specific rotation.