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Synfacts 2020; 16(12): 1453
DOI: 10.1055/s-0040-1706557
Polymer-Supported Synthesis

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

Rezensent(en):
Yasuhiro Uozumi
,
Ryoko Niimi
Chang F, Wang S, Zhao Z, Wang L, Cheng T, Liu G. * Shanghai Normal University, P. R. of China
Enantioselective Dual-Catalysis: A Sequential Michael Addition/Asymmetric Transfer Hydrogenation of α-Nitrosulfone and Enones.

ACS Catal. 2020;
10: 10381-10389
DOI: 10.1021/acscatal.0c01559.
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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).


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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.


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Publikationsverlauf

Artikel online veröffentlicht:
17. November 2020

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