Synthesis of Optically Active,Cyclic alpha-Hydroxy Ketones and 1,2-Diketones from Verbenone Epoxide

摘要

The reactivity of verbenone epoxide (5),a terpenoid from the pinane series,towards different aliphatic and aromatic aldehydes in the presence of natural montmorillonite (askanite-bentonite) clay has been studied.A series of mechanistically different transformations afforded a number of new,optically active,polyfunctional compounds (7,8,10-14,16).These products are potentially interesting syn-thons in asymmetric synthesis.