An efficient TMSOTf-promoted selective triple consecutive
insertions
of tert-butyl isocyanide into aldehydes has been
developed, affording pharmacological interesting 4-cyanooxazoles in
high yields in a one pot manner. The given method encompasses a wide
range of substrates with tert-butyl isocyanide serving
as sources of critical “CN” and “C–NC”
moieties. The versatile transformations of the resulting 4-cyanooxazoles
were demonstrated. The key reaction intermediates for plausible mechanisms
were determined.
A direct
nitration of vinylcyclopropanes is disclosed with Cu(NO3)2 and KI in a regio- and stereoselective manner
to afford nitroalkenes efficiently, where the cyclopropane skeleton
was retained. The given method could be extended to other vinylcycles
as well as biomolecule derivatives with wide substrate scope, good
functionality tolerance, and efficient synthesis modularity. Further
transformations illustrated the obtained products as versatile building
blocks in organic synthesis. The proposed ionic pathway could account
for the untouched small ring and the effect of KI during the reaction.
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