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, cilt.14, sa.11, ss.1489-1493, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 14 Sayı: 11
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1016/s0957-4166(03)00214-3
  • Dergi Adı: TETRAHEDRON-ASYMMETRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1489-1493
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.