Stereospecific synthesis of 2,4-diaxial adamantane and 2,4-di-endo-protoadamantane derivatives via a nitrone intermediate

Abstract

An intramolecular 1,3-dipolar cycloaddition of the bicyclo[3.3.1]non-6-ene nitrone (3) yielded the 2,4-oxa-aza-bridged-protoadamantane (4), -adamantane (5), and 2-ax-amino-4-ax-hydroxyadamantane derivatives (6) in a ratio depending on the substituents and reaction conditions used; reduction of (4) gave the 2-endo-amino-4-endo-hydroxyprotoadamantane derivative (7) in good yield.