Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan.
A new asymmetric entry of the 1,2-aza-Friedel-Crafts reaction catalyzed by a chiral phosphoric acid is described. The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral gamma-butenolid.
Uraguchi
Daisuke
D
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Sorimachi
Keiichi
K
Terada
Masahiro
M