Betti bases are aminoalkylnaphthols that were initially developed back in 1900. Possessing a chiral center and a chiral axis in close proximity to each other, these bases have since been shown to be effective chiral ligands in metal-catalyzed asymmetric chemistry. We have recently begun investigating the possibility of employing Betti bases as iminium ion catalysts. We have devised a concise, six-step synthetic route towards an array of stereodifferentiated Betti bases. A key step towards the preparation of these compounds proved to be the use of silica-bound toluenesulfonic acid as the proton source for the Friedel-Crafts reaction required to generate the key chiral center. The results of these efforts will be discussed.

Betti bases for application in green organocatalysis

245th National Meeting (2013)

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