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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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

Author(s): Luo Mei

Volume 13, Issue 3, 2016

Page: [476 - 482] Pages: 7

DOI: 10.2174/157017941303160407000300

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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.

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