- Turkish Journal of Chemistry
- Vol: 43 Issue: 2
- Chiral 1,4-aminoalkylphenols for enantioselective diethylzinc addition to aldehydes
Chiral 1,4-aminoalkylphenols for enantioselective diethylzinc addition to aldehydes
Authors : Ömer Dilek, Mustafa Ali Tezeren, Tahir Tilki, Erkan Ertürk
Pages : 612-623
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Publication Date : 9999-12-31
Article Type : Makaleler
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