Isothioureas act as efficient Lewis base catalysts in many synthetically useful transformations. Recently, our research group has shown that chiral isothioureas can promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and a-keto-�,?-unsaturated esters via a chiral ammonium enolate intermediate to give anti-dihydropyranones with high diastereo- and enantioselectivity (up to 98:2 dr, up to 99% ee). We now report the expansion of this process to access other pharmaceutically relevant scaffolds with high levels of diastereo- and enantiocontrol. 

New applications of chiral ammonium enolates in organic synthesis

245th National Meeting (2013)

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