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

Authors

ÖMER DİLEK
MUSTAFA ALİ TEZEREN
TAHİR TİLKİ
ERKAN ERTÜRK

DOI

10.3906/kim-1810-78

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 Et$_{2}$Zn addition to benzaldehyde. 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.

Keywords

Asymmetric catalysis, aminoalcohols, aminoalkylphenols, diethylzinc addition

First Page

612

Last Page

623

Recommended Citation

DİLEK, ÖMER; TEZEREN, MUSTAFA ALİ; TİLKİ, TAHİR; and ERTÜRK, ERKAN (2019) "Chiral 1,4-aminoalkylphenols for enantioselective diethylzinc addition to aldehydes," Turkish Journal of Chemistry: Vol. 43: No. 2, Article 20. https://doi.org/10.3906/kim-1810-78
Available at: https://journals.tubitak.gov.tr/chem/vol43/iss2/20