Synthesis of New Chiral and Racemic 1,3-Dioxolanes

Kucuk H. B., Yusufoglu A. S.

JOURNAL OF HETEROCYCLIC CHEMISTRY, cilt.49, sa.5, ss.1066-1070, 2012 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 49 Sayı: 5
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1002/jhet.937
  • Dergi Adı: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1066-1070
  • İstanbul Üniversitesi Adresli: Evet

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, 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 (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-3–12, 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.