Atroposelective Access to Dihydropyridinones with C–N Axial and Point Chirality via NHC-Catalyzed [3 + 3] Annulation

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(15), С. 11299 - 11309

Опубликована: Июль 14, 2023

An N-heterocyclic carbene-catalyzed atroposelective [3 + 3] annulation of enals with 2-aminomaleate derivatives is described. A series substituted dihydropyridones bearing both C-N axis and point chirality were synthesized good diastereo- enantioselectivity under mild conditions. This efficient strategy successfully superpositions an extra chiral element axial backbone, the generated structurally interesting atropisomers may have potential application in drug discovery.

Язык: Английский

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Enantioselective [3 + 3] Annulation–Deoxalation Strategy for Rapid Access to δ-Oxoesters via N-Heterocyclic Carbene Catalysis

Organic Letters, Год журнала: 2024, Номер 26(6), С. 1207 - 1211

Опубликована: Фев. 7, 2024

A new and unprecedented stereoselective synthetic approach to δ-oxoesters derivatives from readily available starting materials has been developed. This method, catalyzed by N-heterocyclic carbene, involves an annulation–deoxalation reaction of alkynyl aldehydes with 2,4-diketoesters proceeds via the chiral α,β-unsaturated acylazolium intermediates. The annulation includes in situ formation dihydropyranones, which undergo ring-opening methanolysis Lewis acid activation, followed deoxalation afford 1,5-ketoesters moderate good yields.

Язык: Английский

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Enantioselective Synthesis of Dihydrothiopyranones via NHC-Catalyzed [3 + 3] Annulation of 2-Bromoenals with β-Oxodithioesters

Organic Letters, Год журнала: 2022, Номер 24(48), С. 8848 - 8853

Опубликована: Ноя. 28, 2022

The N-heterocyclic carbene (NHC)-organocatalyzed [3 + 3] annulation of 2-bromoenals with β-oxodithioesters resulting in the enantioselective synthesis dihydrothiopyranones is presented. chiral α,β-unsaturated acylazoliums generated from and carbenes underwent smooth interception sulfur nucleophiles to furnish heterocycles satisfactory yields/selectivity. regioselective formation over competing dihydropyranones noteworthy.

Язык: Английский

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N-Heterocyclic Carbene-Catalyzed Enantioselective [3 + 2] Annulation of Enals with Vinyl Ketones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(2), С. 1219 - 1226

Опубликована: Янв. 9, 2023

An unprecedented N-heterocyclic carbene (NHC)-catalyzed enantioselective [3 + 2] annulation of enals with vinyl ketones has been achieved. Unlike chalcones, the β-unsubstituted enones, namely, ketones, have remained challenging in terms reactivity, especially enantioselectivity. The disubstituted cyclopentenes were obtained good yields and excellent stereoselectivities presence Ti(OiPr)4.

Язык: Английский

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NHC-catalyzed radical acylation of cycloalkyl silyl peroxides to access 1,6-,1,7-, and 1,8-diketones

Chemical Communications, Год журнала: 2023, Номер 59(88), С. 13175 - 13178

Опубликована: Янв. 1, 2023

An NHC organocatalytic radical acylation of cycloalkyl silyl peroxides with aldehydes was developed for the efficient and rapid synthesis long-chain 1,6-/1,7-/1,8-diketones, especially unsymmetrical ones.

Язык: Английский

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