Organocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan
Journal of the American Chemical SocietyPublished 1 September 2004
Daisuke Uraguchi, Keiichi Sorimachi, Masahiro Terada
Citations353
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion and could be further derivatized to a chiral gamma-butenolid.
Abstract
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.
Keywords
Chemistry
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