Chiral 1,4-aminoalkylphenols for enantioselective diethylzinc addition to aldehydes


DİLEK Ö., TEZEREN M. A., TİLKİ T., ERTÜRK E.

Turkish Journal of Chemistry, vol.43, no.2, pp.612-623, 2019 (SCI-Expanded, Scopus, TRDizin)

  • Publication Type: Article / Article
  • Volume: 43 Issue: 2
  • Publication Date: 2019
  • Doi Number: 10.3906/kim-1810-78
  • Journal Name: Turkish Journal of Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.612-623
  • Isparta University of Applied Sciences Affiliated: Yes

Abstract

Starting from a chiral secondary alcohol, novel enantiopure 1,4-aminoalkylphenols (AAPs) were prepared byexploiting conventional organic transformations such as the Mitsunobu reaction, Eschweiler–Clarke N -methylation, anddemethylation of anisoles. The catalytic activity of the 1,4-AAPs was investigated in enantioselective Et 2 Zn addition tobenzaldehyde. They were found to accelerate the Et 2 Zn addition to benzaldehyde. High yields and enantioselectivities(e.g., 95% yield and 82% ee) were achieved.