Hydroalkoxylation-Initiated Cascade on Sulfone-Tethered Aryl Alkynols Gives Cyclic and Spiro-Heterocyclic β-Ketosulfones,Organic Letters

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Hydroalkoxylation-Initiated Cascade on Sulfone-Tethered Aryl Alkynols Gives Cyclic and Spiro-Heterocyclic β-Ketosulfones
Organic Letters ( IF 4.9 ) Pub Date : 2023-08-10 , DOI: 10.1021/acs.orglett.3c02241
Santosh J Gharpure ₁ , Dipak J Fartade ₁ , Santosh K Nanda ₁ , Shipra Somani ₁

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Serendipitous formation of cyclic β-ketosulfones is observed when sulfone-tethered arylalkynols are reacted with base. The reaction involves a base-promoted propargyl sulfone to the allene isomerization/intramolecular hydroalkoxylation/retro-oxa-Michael/6-endo-trig Michael addition cascade. Sulfone-tethered alkynyl acrylates gave stereoselective access to a diverse array of spirocyclic β-ketosulfone benzofuran/isochroman/indolines and sulfone-tethered bridged bicyclo[3.3.1]nonane. These cyclic β-ketosulfones could be readily elaborated into benzofuran-fused cyclic sulfones and tetracyclic spiroindoline.

中文翻译：

砜系芳基炔醇上的氢烷氧基化引发级联生成环状和螺杂环 β-酮砜

当砜系芳基炔醇与碱反应时，观察到环状 β-酮砜的偶然形成。该反应涉及碱促进的炔丙基砜至丙二烯异构化/分子内加氢烷氧基化/retro- oxa -Michael/6- end - trig Michael加成级联。砜系丙烯酸炔基酯可以立体选择性地获得多种螺环β-酮砜苯并呋喃/异色满/二氢吲哚和砜系桥联双环[3.3.1]壬烷。这些环状β-酮砜可以很容易地加工成苯并呋喃稠合的环状砜和四环螺吲哚啉。

更新日期：2023-08-10

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