Catalytic Asymmetric Domino Michael/Annulation Reaction of Bifunctional Chromone Synthons with β,γ-Unsaturated α-Keto Esters: Rapid Access to Polysubstituted Spirocyclic Hexahydroxanthones

Hao-Jie Zhou; Wei Zhou; Xiong-Li Liu; You-Ping Tian; Jun-Xin Wang; Ying Zhou

doi:10.1055/s-0040-1707340

Synthesis, Table of Contents

Synthesis 2020; 52(20): 3047-3057
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

Hao-Jie Zhou

^aCollege of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, P. R. of China Email: xlliu1@gzu.edu.cn Email: zhouying067@gzy.edu.cn

^bGuizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China

,

Wei Zhou

^bGuizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China

,

Xiong-Li Liu ∗

^aCollege of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, P. R. of China Email: xlliu1@gzu.edu.cn Email: zhouying067@gzy.edu.cn

^bGuizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China

,

You-Ping Tian

^aCollege of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, P. R. of China Email: xlliu1@gzu.edu.cn Email: zhouying067@gzy.edu.cn

,

Jun-Xin Wang

^bGuizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, 550025, P. R. of China

,

Ying Zhou∗

^aCollege of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, P. R. of China Email: xlliu1@gzu.edu.cn Email: zhouying067@gzy.edu.cn

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Abstract

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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 hexahydroxanthones

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References

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Supplementary Material