One-pot highly stereoselective synthesis of cyano aziridines via the CuCl-catalyzed aminochlorination of α,β-unsaturated nitriles and intramolecular S(N) 2 substitution.
An efficient one-pot system has been developed for the synthesis of cyano aziridine by using α,β-unsaturated nitriles as the alkene substrates and N,N-dichloro-p-toluenesulfonamide (4-TsNCl(2) ) as the nitrogen source. A good scope of alkene substrates was achieved for this reaction. The one-pot reaction, via aminohalogenation and intramolecular S(N) 2 substitution, was very convenient to carry out at room temperature without the protection of inert gases. Modest to good yields and excellent have been obtained. This method provides an easy route to the cyano aziridine. The structure of the resulting products has been unambiguously confirmed by X-ray structural analysis.
Mei
Haibo
H
Nanjing University, China.
Yan
Lijun
L
Han
Jianlin
J
Li
Guigen
G
Pan
Yi
Y
D000475:Alkenes / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003486:Cyanides / Q000737:chemistry*; D054879:Halogenation; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D001388:Aziridines; D003486:Cyanides; D009570:Nitriles; D003300:Copper; C029892:cupric chloride