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DOI: 10.1055/s-0036-1589408
Concentration Effect in the Asymmetric Michael Addition of Acetone to β-Nitrostyrenes Catalyzed by Primary Amine Thioureas
Publikationsverlauf
Received: 28. September 2016
Accepted after revision: 07. Oktober 2016
Publikationsdatum:
14. November 2016 (online)
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Dedicated to Professor Dieter Enders on the occasion of his 70th birthday
Abstract
Bifunctional primary amine thiourea (PAT) organocatalysts show remarkable improvement in enantioselectivity and catalytic activity (turnover frequency) in the asymmetric Michael addition of acetone to β-nitrostyrenes upon dilution. Mechanistic investigations indicate that this behavior corresponds to the inhibition of off-cycle catalyst deactivation at low concentration, rather than to the operation of aggregation phenomena at high concentration. Reaction at low concentration (≤0.2 M in β-nitrostyrene) leads to the minimization of catalyst deactivation and, thus, to the optimization of yield and ee of the Michael addition products.
Key words
primary amine thioureas - Michael addition - asymmetric catalysis - organocatalysis - concentration effectSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589408.
- Supporting Information
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