Silyl-Group Boosted Internal Redox Reaction: Hydride Shift from an Aliphatic Secondary Position for the Formation of Six- and Seven-Membered Carbocycles

Organic Letters, Год журнала: 2024, Номер 26(8), С. 1662 - 1666

Опубликована: Фев. 21, 2024

We report a hydride shift/cyclization reaction at the aliphatic secondary position (methylene group). The key to accomplishing this was employment of benzylidene malonate having silyl group β donor carbon. When corresponding malonates were treated with catalytic amount Al(OTf)3, [1,5]-hydride shift from simple proceeded smoothly afford silyl-group substituted tetralin derivatives in excellent chemical yields (up 98%). This system applied formation seven-membered carbocycles via [1,6]-hydride mediated process.

Язык: Английский

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Study on 1,4-hydride shift triggered spirocyclization of arylidene imidazolones: substituent control on formation of indane or tetrahydrobenzazepine systems

Mendeleev Communications, Год журнала: 2025, Номер 35(1), С. 18 - 21

Опубликована: Янв. 1, 2025

Язык: Английский

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Divergent Aromatization of α-Halobenzyl γ-Butenolides Initiated by Selective Enol Protonation to Benzo[c]fluorenones and Naphthalenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 11067 - 11071

Опубликована: Июль 23, 2024

An unprecedented divergent aromatization reaction of α-halobenzyl γ-butenolides has been described for the selective and concise synthesis highly substituted benzo higher π-extended fluorenones, 1,3-disubstituted naphthalenes depending on migration ability quaternary α-substituent. This switch from Ag

Язык: Английский

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Regioselective Decarboxylative Aromatization of Benzonorcaradienes to Substituted 1‐Acylmethyl‐4‐Arylnaphthalenes

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(41)

Опубликована: Июль 31, 2024

Abstract Tf 2 NH‐mediated decarboxylative dearomatization reaction of benzonorcaradiene γ‐ketoacids, in situ generated by intramolecular alkenylation alkynylcyclopropane γ‐ketoacids or their tert ‐butyl esters, has been described for regioselective synthesis polyfunctionalized 1‐acylmethyl‐4‐arylnaphthalenes.

Язык: Английский

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Stereoselective synthesis of 6/7/6-fused heterocycles with multiple stereocenters via internal redox reaction/inverse electron-demand hetero-Diels–Alder reaction sequence

Chemical Communications, Год журнала: 2024, Номер 60(53), С. 6797 - 6800

Опубликована: Янв. 1, 2024

A highly stereoselective synthesis of fused heterocycles with multiple stereocenters

Язык: Английский

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Water-enabled α-C(sp³)–H amination via [1,6]-hydride transfer: green access to diazepino[6,5,4-cd]indoles

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Water-enabled α -C(sp 3 )–H amination of 4-dialkylamino-indole-3-carbaldehydes with primary amines was developed for green synthesis diazepino[6,5,4- cd ]indoles via cascade aldimine condensation/[1,6]-hydride transfer/cyclization.

Язык: Английский

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Quinoline as an Intramolecular Hydride Shuttle in the Deoxygenative Coupling Reaction of Alcohol and the Inert Methyl C(sp³)–H Bond

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

Опубликована: Дек. 9, 2024

Reported herein is the C(sp

Язык: Английский

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