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

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4941 - 4971

Published: Jan. 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.

Language: Английский

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

Organic Letters, Journal Year: 2023, Volume and Issue: 25(12), P. 2058 - 2062

Published: March 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.

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4738 - 4743

Published: May 29, 2024

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

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(19), P. 4043 - 4048

Published: May 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.

Language: 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, Journal Year: 2025, Volume and Issue: 45(2), P. 694 - 694

Published: Jan. 1, 2025

Language: Английский

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

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(20)

Published: May 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.

Language: 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, Journal Year: 2025, Volume and Issue: unknown

Published: June 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.

Language: Английский

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

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 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.

Language: Английский

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

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(4), P. 775 - 782

Published: Dec. 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.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6193 - 6204

Published: April 13, 2024

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

Language: Английский

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