The combination of 2-NsNH2/NCS and MeCN as the nitrogen sources for the regio- and stereoselective formation of imidazolines from α,β-unsaturated ketones |
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Authors: | Cody Timmons Dianjun Chen C. Elizabeth Barney Sameer Kirtane Guigen Li |
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Affiliation: | aDepartment of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA |
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Abstract: | A new nitrogen source combination was found for the regio- and stereoselective diamination of α,β-unsaturated ketones. This combination employs the readily available and inexpensive combination of NCS and 2-NsNH2 as the electrophilic nitrogen source, and acetonitrile as the nucleophilic nitrogen source, respectively. The reaction is easily performed by mixing olefin, 2-NsNH2, NCS and 4 Å molecular sieves in freshly distilled acetonitrile at room temperature. The reaction is chemoselective without the formation of any haloamine side products. A new aziridinium ion formed from enones and 2-NsNHCl is suggested to exist and to react with nitrile via a [2+3] cycloaddition mechanism, which is responsible for the excellent regio-, stereoselectivity of the resulting diamination products. |
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Keywords: | Diamination Diamine NCS N,N-Dichloro-2-nitrobenzenesulfonamide |
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