Stereoselective synthesis of optically active cyclitol precursors via a chemoenzymatic method

Oguzkaya F., Sahin E., Tanyeli C.

TETRAHEDRON-ASYMMETRY, cilt.17, sa.21, ss.3004-3009, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 17 Sayı: 21
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1016/j.tetasy.2006.11.002
  • Dergi Adı: TETRAHEDRON-ASYMMETRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3004-3009
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Racemic alpha'-acetoxy alpha,beta-unsaturated cyclohexanone has been converted to the corresponding enantiomerically enriched alpha'-hydroxylated and acetoxylated compounds with 97% ee via enzymatic resolution with PLE. OSO4-Catalyzed dihydroxylation of enantiomerically enriched alpha'-acetoxylated compound afforded a single diastereomer in 85% chemical yield. The absolute configuration of 2,3,6-triacetoxycylohexanone was determined by X-ray diffraction analysis. Subsequent Luche reduction allowed us to obtain corresponding syn-type cyclitol precursors in a highly stereoselective manner as expected. (c) 2006 Elsevier Ltd. All rights reserved.