2-(1,3-Dioxan-2-yl)ethylsulfonyl group: a new versatile protecting and activating group for amine synthesis.
[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.
Sakamoto
Izumi
I
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Izumi
Norimasa
N
Yamada
Taeko
T
Tsunoda
Tetsuto
T