Chiral auxiliaries based on camphor have been used successfully used in a wide variety of reactions. The rigid camphor ring system leads to derivatives with very defined conformations: For example, the <i>p</i>-nitrobenzoate ester of 3-<i>endo</i>-benzylisoborneol has a crystal conformation in which the two aromatic rings are p-stacked. We are undertaking a systematic exploration of the synthesis and use of 3-benzylisobornylamine derivatives as chiral organocatalysts  for Diels-Alder, Friedel-Crafts and Michael additions, and a phopshonate derivative as a chiral auxiliary for aldol additions of lithium enolates. Our progress to date will be discussed.

3-Benzylidenecamphor derivatives and their conversion into chiral auxiliaries and organocatalysts

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.