Betti bases are aminoalkylnaphthols that were initially developed back in 1900 by Mario Betti. 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. During our investigations into the preparation of Betti bases, we developed a new aza-Friedel-Crafts-like reaction to generate the key chiral center. Instrumental to the success of this reaction was the use of silica-?bound toluenesulfonic acid as a Bronsted acid catalyst. We have recently begun exploring the scope of this aza-Friedel Crafts-like reaction, using chiral imines to diastereoselectively form the corresponding amine products. These compounds have potential utility as pharmaceutical building blocks. The results of these studies will be discussed.

Diastereoselective, Br�nsted acid-catalyzed, aza-Friedel Crafts-like reaction between aryl compounds and imines

247th National Meeting (2014)

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