Abstract
Compounds incorporating a 4-aza-8-oxabicyclo[3.2.1]oct-6-en-2-one moiety, which were
prepared by a tandem carbenoid carbonyl ylide cyclization/[3+2]-cycloaddition reaction
from ethyl 2-diazo-3-oxo-4-phthalimidobutanoates, undergo a nucleophile-induced two-bond
ring cleavage when treated with protic heteronucleophiles. In this manner, tetrasubstituted
furantricarboxylates, tethered with α-amino acids, esters, thioesters, and amides
by a 2-carbonylphenyl moiety, are obtained.
Key words
diazo compounds - carbonyl ylides - carboxamides - cycloaddition - furan