An ATP-Cu(ii) catalyst efficiently catalyzes enantioselective Michael reactions in water

Biological hybrid catalysts have emerged as promising approaches to achieve enantioselective reactions in aqueous media. Enantioselective Michael reactions are one of the most important carbon-carbon bond formation reactions in organic synthesis, yet their aqueous-phase catalysis remains challenging. Herein, a single nucleotide-based catalyst (ATP center dot Cu2+) has been constructed using ATP and Cu2+ ions and catalyzes Michael reactions in aqueous media with high reactivities and good enantioselectivities up to 83% ee. The enantioselective catalytic performances of ATP center dot Cu2+ originate from specific binding between ATP and Cu2+ ions that exhibit both pH-dependent and temperature-dependent behaviors. The ATP center dot Cu2+ has been demonstrated to be successfully applied to a wide spectrum of enone substrates and carbon nucleophiles.

Automated summary

In this study, a single nucleotide-based catalyst (ATP·Cu2+) was successfully constructed and demonstrated to catalyze enantioselective Michael reactions in aqueous media with high reactivities and good enantioselectivities up to 83% ee. The enantioselective catalytic performances of ATP·Cu2+ originate from specific binding between ATP and Cu2+ ions that exhibit both pH-dependent and temperature-dependent behaviors. The ATP·Cu2+ catalyst has been successfully applied to a wide spectrum of enone substrates and carbon nucleophiles.