Nature, our teacher! The natural alkaloids quinine (Q) and quinidine (QD) serve as efficient bifunctional organocatalysts in the asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides (see scheme). Very high selectivity is observed in this one-step construction of highly functionalized compounds with two adjacent stereogenic centers from commercially available precursors. R1,R3=alkyl, aryl, O-alkyl; R2=alkyl, Bn; R4=Bn.
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Bartoli et al. (2006) studied this question.
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