Title:The Cyanation of Prochiral Aldehydes with Chiral Copper Complexes of R-(+)/S-(-) -α-Ethylphenyl Amine in Methanol
VOLUME: 13 ISSUE: 3
Author(s):Luo Mei
Affiliation:Hefei University of Technology, Department of Chemical Engineering, Hefei, 230009, China.
Keywords:Cyanation, chiral copper complexes, R-(+)/S-(-) -α-ethylphenyl amine, methanol, acetols, cyanohydrin.
Abstract:Interesting and unexpected results on the cyanation of prochiral aldehydes catalyzed by chiral copper
complexes of R-(+)/(S)-(-) α-ethylphenyl amine (I/II) in anhydrous methanol are presented. The cyanation reaction
with chiral copper complexes of R-(+)/S-(-) α-ethylphenyl amines, acetols in methanol perform to afford a series of
chiral products such as amines and acetonitriles (compounds 4-6, 8, 10 and 11). The obtained products are fully
characterized by NMR, IR and X-ray analysis. The proposed mechanism for the formation of a series of chiral
products can be concluded that methanol firstly promotes the decomposition of the copper complexes bearing R-
(+)/S-(-) α-ethylphenyl amines to the ligand R-(+)/ S-(-)-α-ethylphenyl amine, which then conjugated with the initial
TMS ether of the cyanohydrin or cyanohydrin to afford the chiral compounds 4-6, 8, 10 and 11.
