Iron(III) trifluoroacetate [Fe(O2CCF3)(3)] catalyzed epoxide opening with amines

Erturk E., DEMİR A. G.

ARKIVOC, pp.160-171, 2008 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Publication Date: 2008
  • Journal Name: ARKIVOC
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.160-171
  • Keywords: epoxide, epoxide opening, amino alcohol, iron, solvent-free, green chemistry, HYDROLYTIC KINETIC RESOLUTION, AROMATIC-AMINES, EFFICIENT METHOD, MESO-EPOXIDES, ASYMMETRIC AMINOLYSIS, ALCOHOLS, MILD, CLEAVAGE, TRIFLATE, ANILINES
  • Middle East Technical University Affiliated: Yes

Abstract

Non-hygroscopic, non-toxic, and readily available iron(III) trifluoroacetate [Fe(O2CCF3)(3)] was found to be a highly regioselective catalyst for the ring opening of a wide variety of epoxides with diverse amines under solvent-free conditions. The stereospecific ring opening of (R)-styrene oxide (4) with p-anisidine (2b) in the presence of 1 mol% of Fe(O2CCF3)(3) gave 2-(p-methoxyphenyl-amino)-2-phenylethanol (5b) in enantiopure form (> 99 % ee) within 60 minutes.