3-Benzylidenecamphor Derivatives and Their Conversion Into Chiral Auxiliaries and Organocatalysts
Hartfield, Phillip J.
Kennedy, Michael K.
Lewis, David E.
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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.