Ag(i)-catalyzed asymmetric (2+4) annulation reaction of 5-alkenyl thiazolones: synthesis of enantioenriched spiro[cyclohexenamines-thiazolones]

Chemical Communications, Год журнала: 2024, Номер 60(68), С. 9062 - 9065

Опубликована: Янв. 1, 2024

We report the first metal-catalyzed (2+4) annulation of 5-alkenyl thiazolones and dicyanoalkylidenes, delivering spiro[cyclohexenamines-thiazolones] with high stereoselectivities.

Язык: Английский

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Enantioselective Dearomative [4+2] Cycloaddition Reaction of 1‐Naphthols with In‐Situ Generated ortho‐Quinone Methides

Chemistry - A European Journal, Год журнала: 2023, Номер 29(69)

Опубликована: Сен. 14, 2023

We disclose a catalytic, enantioselective dearomative reaction of non-functionalized 1-naphthols, which poses synthetic challenge to organic chemists because the relative ease rearomatization via elimination proton. In this work, direct dearomatization 1-naphthols was achieved through chiral phosphoric acid (CPA) catalyzed [4+2] cycloaddition with in-situ generated ortho-quinone methides (o-QMs). The reported convergent method allows use readily available simple without pre-functionalization, furnishing variety naphthopyran derivatives in good yields (up 96 %) and moderate excellent enantioselectivities >99 % ee) under mild conditions. observed regio-, diastereo-, are keys success current strategy utilizing o-QM as diene surrogates, combination CPA catalysis.

Язык: Английский

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Base‐Catalyzed Decarboxylative Amination of In‐situ Generated ortho‐Quinone Methides: Synthesis of Benzyl Amines

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Июль 27, 2024

Abstract In this paper, a direct access to benzylic amines from in‐situ generated ortho ‐quinone methides ( o ‐QMs) and isocyanate/isothiocyanate via decarboxylation is described. This base‐catalyzed methodology has high functional group tolerance shows wide range of substrate scopes, where H 2 O as nucleophile for product formation. The products are insensitive air moisture, which makes synthetic strategy more efficient the construction various benzyl amine derivatives.

Язык: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 421 - 484

Опубликована: Янв. 1, 2024

Язык: Английский

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