Synthesis of Amino-Substituted Indanes and Tetralins via Consecutive Multibond-Forming Tandem Processes

A rapid and general approach for
the synthesis of amino-substituted
indanes and tetralins from readily available alkyne-derived allylic
alcohols via consecutive multibond-forming tandem processes has been
developed. In the first one-pot tandem process, a series of cyclic
dienes were prepared using an Overman rearrangement under thermal
conditions, followed by a ruthenium­(II)-catalyzed ring closing enyne
metathesis reaction. The resulting exo-dienes were
then subjected to a second one-pot tandem process involving a highly
regioselective Diels–Alder reaction with alkynes, quinones
or nitriles and a subsequent oxidation step to give a diverse library
of C-1 amino-substituted indanes and tetralins in good overall yields.