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


Dilek O., Tezeren M. A. , TİLKİ T. , Erturk E.

TURKISH JOURNAL OF CHEMISTRY, vol.43, no.2, pp.612-623, 2019 (Journal Indexed in SCI) identifier

  • Publication Type: Article / Article
  • Volume: 43 Issue: 2
  • Publication Date: 2019
  • Doi Number: 10.3906/kim-1810-78
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.612-623

Abstract

Starting from a chiral secondary alcohol, novel enantiopure 1,4-aminoalkylphenols (AAPs) were prepared by exploiting conventional organic transformations such as the Mitsunobu reaction, Eschweiler-Clarke N-methylation, and demethylation of anisoles. The catalytic activity of the 1,4-AAPs was investigated in enantioselective Et2Zn addition to benzaldehyde. They were found to accelerate the Et2Zn addition to benzaldehyde. High yields and enantioselectivities (e.g., 95% yield and 82% ee) were achieved.