Synthesis of New Chiral and Racemic 1,3-Dioxolanes


Kucuk H. , Yusufoglu A.

JOURNAL OF HETEROCYCLIC CHEMISTRY, cilt.49, ss.1066-1070, 2012 (SCI İndekslerine Giren Dergi)

  • Cilt numarası: 49 Konu: 5
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1002/jhet.937
  • Dergi Adı: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Sayfa Sayısı: ss.1066-1070

Özet

A series of chiral 1,3-dioxolanes, 3-12, with > 99% ee values, have been synthesized. This is the first study of chiral ketalization reaction starting from ketones with aryl, monosubstituted aryl, and long alkyl chains (C-11-AC(13)). Their ee values were determined by chiral high-performance liquid chromatography (HPLC) on Chiralcel OD column, using their racemic 1,3-dioxolanes rac-3-12, which were also synthesized for the first time. These chiral and racemic 1,3-dioxolanes were characterizated by infrared, NMR (H-1, C-13), mass spectrometry, elemental analysis, optical rotation, and chiral HPLC.

A series of chiral 1,3-dioxolanes, 312, with >99% ee values, have been synthesized. This is the first study of chiral ketalization reaction starting from ketones with aryl, monosubstituted aryl, and long alkyl chains (C11—AC13). Their ee values were determined by chiral high-performance liquid chromatography (HPLC) on Chiralcel OD column, using their racemic 1,3-dioxolanes rac-312, which were also synthesized for the first time. These chiral and racemic 1,3-dioxolanes were characterizated by infrared, NMR (1H, 13C), mass spectrometry, elemental analysis, optical rotation, and chiral HPLC.