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Synthesis 2022; 54(07): 1785-1792
DOI: 10.1055/s-0040-1719863
DOI: 10.1055/s-0040-1719863
paper
Highly Enantioselective Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters Catalyzed by Squaramide Organocatalyst
We are grateful for the financial support of the Natural Science Foundation of Henan Province (No. 202300410188), Training Plan for Young Key Teachers in Colleges and Universities in Henan Province (2021GGJS173) and the Key Scientific Research Project of Colleges and Universities of Henan Province (No. 20A150020).
Abstract
A new tertiary amine-squaramide organocatalyst has been developed and applied to the asymmetric Michael addition of cyclic diketones to β,γ-unsaturated α-keto esters. The catalyst system performed well with a low catalyst loading of 1 mol% under mild reaction conditions. A series of synthetically and pharmaceutically useful chiral bicyclic compounds were obtained in high yields (up to 97%) with excellent enantioselectivities (up to 99 % ee). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained.
Key words
Michael addition - organocatalysis - tertiary amine-squaramide - cyclic diketone - β,γ-unsaturated α-keto estersSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719863.
- Supporting Information
Publikationsverlauf
Eingereicht: 01. September 2021
Angenommen nach Revision: 17. November 2021
Artikel online veröffentlicht:
10. Januar 2022
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