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The Cyanation of Prochiral Aldehydes with Chiral Copper Complexes of R-(+)/S-(-) -α -Ethylphenyl Amine in Methanol

[ Vol. 13 , Issue. 3 ]

Author(s):

Luo Mei   Pages 476 - 482 ( 7 )

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.

Keywords:

Cyanation, chiral copper complexes, R-(+)/S-(-) - α-ethylphenyl amine, methanol, acetols, cyanohydrin.

Affiliation:

Hefei University of Technology, Department of Chemical Engineering, Hefei, 230009, China.



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