Enantiopure cis- and trans-2-(2-Aminocyclohexyl)phenols: Effective Preparation, Solid-State Characterization, and Application in Asymmetric Organocatalysis


TEZEREN M. A. , YESIL T. A. , Zorlu Y., TİLKİ T. , ERTURK E.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, cilt.2018, ss.7017-7032, 2018 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 2018 Konu: 48
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1002/ejoc.201801445
  • Dergi Adı: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Sayfa Sayıları: ss.7017-7032

Özet

Effective synthesis of cis- and trans-2-(2-methoxyphenyl)cyclohexylamine as well as their multigram-scale optical resolution by diastereomeric salt formation with dibenzoyl tartaric acid have been described. Assignment of absolute configurations to the enantiomers has been made by X-ray crystallography. Starting from the resolved precursor, diverse aminoalkylphenols (AAPs) having primary, secondary, and tertiary amine group as well as a quaternary ammonium phenol have been prepared as potential bifunctional organocatalysts based on the cyclohexane backbone. We furthermore report herein that AAPs carrying a primary amine and a phenolic hydroxyl group can catalyze the direct aldol reaction with high activity and setereoselectivity, and thus up to 97 % yield, 90:10 syn/anti diastereomeric ratio, and 80 % enantiomeric excess can be achieved.