Asymmetric synthesis of new chiral 1,2-and 1,3-diols


Yildiz T. , Yusufoglu A. S.

MONATSHEFTE FUR CHEMIE, vol.144, no.2, pp.183-190, 2013 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 144 Issue: 2
  • Publication Date: 2013
  • Doi Number: 10.1007/s00706-012-0792-7
  • Title of Journal : MONATSHEFTE FUR CHEMIE
  • Page Numbers: pp.183-190

Abstract

Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine–BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, 1H and 13C NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine–BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.

Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.