3-Benzylidenecamphor Derivatives and Their Conversion Into Chiral Auxiliaries and Organocatalysts

Abstract

The rigid camphor system with its well-defined geometry potentially possess all the key features required for a highly effective chiral auxiliary. This has been realized by Oppolzer, who devel¬oped three general exo-substituted bornane de¬rivatives for use in a wide variety of reactions. Helmchen has also developed endo-substituted bornane-base alcohols. In earlier work, we demonstrated that the electronical¬ly complementary aromatic rings of 3-endo-p-methoxy¬benzylisobornyl p-nitrobenzoate strongly p-stack, which should make these compounds excellent chiral auxiliaries for conjugate additions and Diels-Alder cycloadditions.