Construction of Functionalized 2H-Pyran-2-ones via N-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Alkynyl Esters with Enolizable Ketones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(3), P. 1836 - 1843

Published: Jan. 25, 2023

A new synthesis of functionalized 2H-pyran-2-ones has been developed through N-heterocyclic carbene-catalyzed formal [3 + 3] annulation alkynyl esters with enolizable ketones. The key to the success this protocol relies on use an NHC instead a tertiary amine as catalyst. This also features broad substrate scope and mild metal-free conditions, offering simple rapid access target molecules in highly regioselective manner.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 11299 - 11309

Published: July 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.

Language: Английский

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

Organic Letters, Journal Year: 2022, Volume and Issue: 24(48), P. 8848 - 8853

Published: Nov. 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.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(2), P. 1219 - 1226

Published: Jan. 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.

Language: Английский

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Construction of axially chiral styrene-type allylaminesviachiral phosphoric acid-catalyzed asymmetric reductive amination

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(3), P. 764 - 770

Published: Dec. 20, 2021

The first enantioselective synthesis of axially chiral styrene-type allylamines through phosphoric acid mediated atroposelective reductive amination 1-enal substituted 2-naphthols is achieved.

Language: Английский

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