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Synthesis 2020; 52(20): 3047-3057
DOI: 10.1055/s-0040-1707340
DOI: 10.1055/s-0040-1707340
paper
Catalytic Asymmetric Domino Michael/Annulation Reaction of Bifunctional Chromone Synthons with β,γ-Unsaturated α-Keto Esters: Rapid Access to Polysubstituted Spirocyclic Hexahydroxanthones
We are grateful for the financial support from the National Natural Science Foundation of China (NSFC; 81760625 and 81660576), the Key Supported Discipline of Guizhou Provence (GNYL[2017]008), and the Natural Science Research Project of Guizhou Provincial Education Office ([2020]1Z074, [2019]1402, [2017]5609, and [2015]4032).Further Information
Publication History
Received: 07 March 2020
Accepted after revision: 25 June 2020
Publication Date:
28 July 2020 (online)
Abstract
A thiourea-catalyzed asymmetric domino Michael/annulation process was devised employing bifunctional oxindole-chromones as C4 synthons and β,γ-unsaturated α-keto esters as C2 synthons. This reaction enables the highly diastereo- and enantioselective synthesis of a range of biologically relevant spirocyclic hexahydroxanthones with one quaternary and four tertiary stereogenic centers, also featuring an intriguing combination of two privileged motifs, including hexahydroxanthone and oxindole substructures, in good yields (up to 76%) and excellent stereoselectivities (up to >99% ee and >20:1 dr). Moreover, using β,γ-unsaturated α-keto esters as the C2 building blocks, which are different from enone substrates such as chalcone and benzalacetone, with the reversible Michael reaction further expanded the scope of the method. In addition, scale-up also demonstrated the applicability of this protocol.
Key words
Michael addition - annulations - oxindoles - chromones - C4 synthons - β,γ-unsaturated α-keto esters - spirocyclic hexahydroxanthonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707340.
- Supporting Information
- CIF File
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11 CCDC 1982865 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.