Isothiourea-Catalyzed Enantioselective Synthesis of trans -3,4-Dihydrothiopyranones: Harnessing Thiochalcones as Original Michael Acceptors - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2023

Isothiourea-Catalyzed Enantioselective Synthesis of trans -3,4-Dihydrothiopyranones: Harnessing Thiochalcones as Original Michael Acceptors

Résumé

Highly enantioselective formal (4 + 2)-cycloaddition between carboxylic acids and thiochalcones promoted by (+)-HBTM-2.1 isothiourea organocatalyst has been reported. The methodology relied on the generation of C1-ammonium enolate intermediates and proceeded through a nucleophilic 1,4-addition-thiolactonization cascade. It enabled the stereocontrolled preparation of sulfur-containing δ-thiolactones in good yields, moderate diastereoselectivity and excellent enantiomeric excess (up to 99%). This annulation benefited from the peculiar reactivity of uncommon electron-rich thiochalcones used as Michael acceptors.
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hal-04295648 , version 1 (20-11-2023)

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Géraldine Masson, Damien Bouchet, Elsa van Elslande. Isothiourea-Catalyzed Enantioselective Synthesis of trans -3,4-Dihydrothiopyranones: Harnessing Thiochalcones as Original Michael Acceptors. Organic Letters, 2023, 25 (28), pp.5395-5399. ⟨10.1021/acs.orglett.3c02011⟩. ⟨hal-04295648⟩
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