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Synthesis of Highly Enantiomerically Enriched Arenesulfonic Acid 2-Hydroxy Esters via Kinetic Resolution of Terminal Epoxides

속도론적 분할법을 통한 말단 에폭사이드로부터 고광학순도의 아렌술폰산 2-하이드록시 에스터의 합성

  • Lee, Yae Won (Department of Chemical Engineering, Inha University) ;
  • Yang, Hee Chun (Department of Chemical Engineering, Inha University) ;
  • Kim, Geon-Joong (Department of Chemical Engineering, Inha University)
  • 이예원 (인하대학교 화학공학과) ;
  • 양희천 (인하대학교 화학공학과) ;
  • 김건중 (인하대학교 화학공학과)
  • Received : 2016.07.08
  • Accepted : 2016.08.16
  • Published : 2016.10.10

Abstract

This paper describes the very efficient and highly enantioselective ring opening of terminal epoxides with alkyl and arene sulfonic acid. The dinuclear chiral (salen) Co complexes bearing Lewis acids of Al, Ga and In catalyze the reaction enantioselectively in the presence of tetrabutylammonium chloride using tert-butyl methyl ether as a solvent. The variation of the anion of the tetra butyl ammonium salt has significant impact on the reactivity and selectivity of the asymmetric ring opening of phenyl glycidyl ether with p-toluenesulfonic acid. The order of reactivity and selectivity was found to be $Cl^-$ > $l^-$ > $Br^-$ > $OH^-$. Strong synergistic effects of the different Lewis acid centers of Co-Al, Co-Ga and Co-In complexes were observed in the catalytic process. The dinuclear chiral salen catalyst containing $AlCl_3$ was found to be most active and highly enantioselective (91% ee).

Acknowledgement

Grant : BK21플러스

Supported by : 인하대학교

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