Strained cycloalkanols in C–C bond formation reactions: a boon in disguise!

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(19), С. 4941 - 4971

Опубликована: Янв. 1, 2023

A summary of the various ring opening reactions strained and unstrained cycloalkanols is elaborated in present review. Key emphasis on reactivities pertaining to cyclopropanols, cyclobutanols higher analogues provided.

Язык: Английский

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Arylation of Cyclopropanol with Pyrrole: Asymmetric Synthesis of Indolizidine 167B, Indolizidine 209D, and Monomorine I

Organic Letters, Год журнала: 2023, Номер 25(12), С. 2058 - 2062

Опубликована: Март 17, 2023

A Fe(NO3)3-mediated ring-opening arylation of cyclopropanol with the electron-rich pyrrole has been developed, which might proceed through oxidative radical ring opening followed by cyclization to motif and then aromatization. This method enables direct without prefunctionalization thus allows rapid access a diverse array chiral 5,6,7,8-tetrahydroindolizines from easily available amino acid esters. The synthetic utility demonstrated asymmetric synthesis alklaoids (-)-indolizidine 167B, (+)-indolizidine 209D, (+)-monomorine I, natural product analogue.

Язык: Английский

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Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles

Organic Letters, Год журнала: 2024, Номер 26(22), С. 4738 - 4743

Опубликована: Май 29, 2024

A concise synthetic approach to medicinally relevant pyrroloindolones and related fused heterocycles is reported via the diastereoselective

Язык: Английский

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Ring-Opening Coupling of Cyclopropanol with 1,2,3-Triazole for the Synthesis of Fused Triazoles

Organic Letters, Год журнала: 2024, Номер 26(19), С. 4043 - 4048

Опубликована: Май 2, 2024

A radical ring-opening arylation of cyclopropanol with 1,2,3-triazole has been achieved. This synthetic protocol provides straightforward access to a wide range structurally diverse and chiral 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridines high efficiency from readily available cyclopropanols.

Язык: Английский

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Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 694 - 694

Опубликована: Янв. 1, 2025

Язык: Английский

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Ru(II)‐Catalyzed C‐H Alkylation of Indoles at the C‐3 Position with Coumarin‐3‐Carboxylic Acids

ChemistrySelect, Год журнала: 2025, Номер 10(20)

Опубликована: Май 1, 2025

Abstract A ruthenium(II)‐catalyzed C3‐selective C─H activation of indoles bearing a pyridyl or pyrimidine directing group and subsequent conjugated/decarboxylative addition to coumarin‐3‐carboxylic acids has been demonstrated. This protocol efficiently afforded variety coumarin‐containing with excellent site selectivity, satisfactory product yields, functional tolerance.

Язык: Английский

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Synthesis of 3‐Hydroxyfluorenones Based on the Cascade Reaction of Aryl Enaminones with Benzyl Substituted Cyclopropanols

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 4, 2025

Comprehensive Summary Presented herein is a novel synthesis of 3‐hydroxyfluorenones through the cascade reaction aryl enaminones with benzyl substituted cyclopropanols. The formation product initiated by introduction an enone moiety onto enaminone cyclopropanol as homoenolate precursor C−H bond activation, followed intramolecular enamine Michael addition, enol amine elimination and aromatization‐driven oxidative dehydrogenation. To our knowledge, this should be first example for specific 3‐hydroxyfluorenone derivatives via simultaneous both indenone phenol scaffolds C−H/C−C/C−N activation three C−C formation. In general, newly developed protocol features easily accessible substrates, synthetically pharmaceutically valuable products, unique pathway, good compatibility various functional groups ready scalability.

Язык: Английский

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Zinc‐Mediated Diastereoselective Annulation of Cyclopropanols with Alkylidenemalononitriles via Enolized Homoenolate

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Апрель 13, 2023

Abstract A zinc‐mediated annulation reaction between cyclopropanols and alkylidenemalononitriles is reported. The promoted in the presence of Et 2 Zn 1,4‐diazabicyclo[2.2.2]octane (DABCO) DMSO at 80 °C, affording cyclopropane‐fused 6‐amino‐3,4‐dihydro‐2 H ‐pyran‐5‐carbonitrile derivatives moderate to good yields with high diastereoselectivity. proposed involve an enolized homoenolate as key reactive intermediate, which generated through ring opening zinc cyclopropoxide enolization resulting homoenolate. enolate moiety this species undergoes Michael addition alkylidenemalononitrile, followed by closure α‐functionalized intramolecular cyclization one cyano groups.

Язык: Английский

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Rh(iii)-catalyzed [4 + 1] cyclization of aryl substituted pyrazoles with cyclopropanols via C–H activation

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 21(4), С. 775 - 782

Опубликована: Дек. 19, 2022

A rhodium-catalyzed formal [4 + 1]-cyclization reaction of aryl substituted pyrazoles with cyclopropanols via C-H bond activation/cyclization processes to selectively construct a series carbonyl functionalized pyrazolo[5,1-a]isoindoles is described. The features good functional group compatibility and broad substrate scope respect both cyclization components up 84% yields. Mechanistic studies indicated that the cleavage might be rate-determining step in this transformation.

Язык: Английский

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Synthesis of Vicinal anti-Amino Alcohols from N-tert-Butanesulfinyl Aldimines and Cyclopropanols

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6193 - 6204

Опубликована: Апрель 13, 2024

The stereoselective synthesis of vicinal amino alcohols derivatives from 1-substituted cyclopropanols and chiral

Язык: Английский

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