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C  2 -symmetric bisamidines  8  have been tested as chiral Brønsted bases in the Diels-Alder reaction of anthrones and  N -substituted maleimides. High yields of cycloadducts and significant asymmetric inductions up to 76%  ee  are accessible. The proposed mechanism involves proton transfer between anthrone and bisamidine, association of the resulting ions and finally a cycloaddition step stereoselectively controlled by the chiral ion pair.

C 2-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones

C ₂-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones