12/17/11 - Metal Reduction of Conjugated 2-Decalones

   As a means to regeochemically select an enolate in a decalone it is quite easy if there is a substitution at the Beta carbon.  All that is needed is a lithium solution with liquid ammonia in the presence of tert-butanol to provide protons.  These reagents create a solution of electrons which radically charge the beta position which then is pushed up to the alpha position and creating the enolate as the other negative charge is located on the oxygen, which is chelated to the lithium metal.