Chemoenzymatic synthesis of both enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one

Demir A., Aybey A., Sesenoglu O., Polat F.

TETRAHEDRON-ASYMMETRY, vol.14, no.11, pp.1489-1493, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 14 Issue: 11
  • Publication Date: 2003
  • Doi Number: 10.1016/s0957-4166(03)00214-3
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1489-1493
  • Middle East Technical University Affiliated: Yes

Abstract

4-Oxo-3,4-dihydro-2-chromen-3-yl acetate is synthesized using manganese(III)acetate starting from 2,3-dihydro-4H-chromen-4-one. K2CO3 mediated hydrolysis of 4-oxo-3,4-dihdro-2-chromen-3-yl acetate furnished 3-hydroxy-2,3-dihydro-4H-chromen-4-one in high yield. The enantioselective hydrolysis of (+/-)-4-oxo-3,4-dihydro-2-chromen-3-yI acetate in various organic solvent-phosphate buffer (pH7) systems and enantioselective transesterification of (+/-)-3-hydroxy-2,3-dihydro-4H-chromen-4-one in organic solvents was investigated by screening a range of lipases. The lipase Amano PS, PPL, PLE and CCL-catalyzed asymmetric ester hydrolysis and transesterification afforded the enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one and 4-oxo-3,4-dihydro-2-chromen-3-yI acetate with high enantiomeric excess (up to 97% ee) and in good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.