2-(1,3-Dioxan-2-yl)ethylsulfonyl group: a new versatile protecting and activating group for amine synthesis |
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Authors: | Sakamoto Izumi Izumi Norimasa Yamada Taeko Tsunoda Tetsuto |
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Institution: | Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan. |
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Abstract: | reaction: see text] 2-(1,3-Dioxan-2-yl)ethylsulfonyl (Dios) chloride was synthesized and used as a new versatile sulfonating agent for amines. Primary and secondary amines were sulfonated very easily in excellent yields with Dios chloride. N-Nonsubstituted and N-monosubstituted Dios-amides, activated amines, were alkylated satisfactorily under new Mitsunobu conditions utilizing (cyanomethylene)tributylphosphorane (CMBP). The Dios group is very stable under basic and reductive conditions and is removed by heating in a hot aqueous solution of trifluoroacetic acid. |
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