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Synfacts 2016; 12(10): 1097
DOI: 10.1055/s-0036-1589216
DOI: 10.1055/s-0036-1589216
Polymer-Supported Synthesis
Asymmetric Michael and Aldol Reactions with a Supported Chiral Diamine
Ying A, * Liu S, Li Z, Chen G, Yang J, Yan H, Xu S. * Taizhou University, Nankai University, Tianjin, and Tianjin University, P. R. of China
Magnetic Nanoparticles-Supported Chiral Catalyst with an Imidazolium Ionic Moiety: An Efficient and Recyclable Catalyst for Asymmetric Michael and Aldol Reactions.
Adv. Synth. Catal. 2016;
358: 2116-2125
Magnetic Nanoparticles-Supported Chiral Catalyst with an Imidazolium Ionic Moiety: An Efficient and Recyclable Catalyst for Asymmetric Michael and Aldol Reactions.
Adv. Synth. Catal. 2016;
358: 2116-2125
Further Information
Publication History
Publication Date:
19 September 2016 (online)
Key words
asymmetric catalysis - Michael addition - aldol reaction - organocatalysis - magnetic nanoparticles
Significance
A magnetic nanoparticle supported chiral aminocyclohexane 1 was prepared according to eq. 1. Asymmetric Michael and aldol reactions were carried out in the presence of 1 and DMAP in water at room temperature (eqs. 2 and 3, respectively) to give the corresponding adducts in ≤94% yield and ≤100% ee.
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Comment
The organocatalyst 1 was characterized by FT-IR, XRD, TEM, VSM, TG, and elemental analyses. In the reaction of nitrostyrene with isobutyraldehyde, the catalyst was magnetically recovered and reused four times without significant loss of its catalytic performance (fourth reuse: 83% yield, 95% ee).
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