Regioselective and Stereoselective Addition of Formaldehyde to Monoterpenones

Article abstract of DOI:10.1002/ardp.19853180315

The hydroxymethyl derivatives of isopinocamphone, isocaranone, carvomenthone and menthone were prepared using formaldehyde and alkaline catalysis.The preferential position of attack is the more highly branched carbon atom of the enolate.The addition of formaldehyde proceeds regio- and stereoselectively with the bicyclic monoterpenones and regioselectively only with the monocyclic monoterpenones.