One-Pot Two-Step Catalytic Asymmetric Michael Addition/Hydrogenation

Key words

dual catalysis - one-pot synthesis - organocatalysis - ruthenium catalysis - asymmetric catalysis - Michael addition

Significance

A one-pot two-step asymmetric ­Michael addition–transfer hydrogenation co-catalyzed by an immobilized organocatalyst [SA@HSMSN (Cat. A)] and a Ru complex catalyst {[Ru]@HSMSN/HP (Cat. B)} was developed. The reaction of enone 1 and nitro sulfone 2 in the presence of Cat. A, Cat. B, and HCO₂Na gave the corresponding alcohols 4 in excellent chemical yields and with high diastereoselectivity (96–99% ee).

Comment

Squaramide and MesRuArDPEN were immobilized in hollow-shell-mesostructured silica nanoparticles without or with a hydrophilic polymer coating to form Cat. A and Cat. B, respectively. Cat. A promoted the Michael addition at –35 °C, and Cat. B catalyzed the transfer hydrogenation at 35 °C, to realize temperature-dependent control of the sequential dual-catalytic process.

Publication History

Article published online:
17 November 2020