A Vinyl Cyclopropane Ring Expansion and Iridium‐Catalyzed Hydrogen Borrowing Cascade

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Abstract: A vinyl cyclopropane rearrangement embedded in an iridium‐catalyzed hydrogen borrowing reaction enabled the formation of substituted stereo‐defined cyclopentanes from Ph* methyl ketone and cyclopropyl alcohols. Mechanistic studies provide evidence for the ring‐expansion reaction being the result of a cascade based on oxidation of the cyclopropyl alcohols, followed by aldol condensation with the pentamethyl phenyl‐substituted ketone to form an enone containing the vinyl cyclopropane. Subsequent single electron transfer (SET) to this system initiates a rearrangement, and the catalytic cycle is completed by reduction of the new enone. This process allows for the efficient formation of diversely substituted cyclopentanes as well as the construction of complex bicyclic carbon skeletons containing up to four contiguous stereocentres, all with high diastereoselectivity.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: A Vinyl Cyclopropane Ring Expansion and Iridium‐Catalyzed Hydrogen Borrowing Cascade ; volume:59 ; number:28 ; year:2020 ; pages:11339-11344 ; extent:6
Angewandte Chemie / International edition. International edition ; 59, Heft 28 (2020), 11339-11344 (gesamt 6)

Creator: Wübbolt, Simon
Cheong, Choon Boon
Frost, James R.
Christensen, Kirsten E.
Donohoe, Timothy J.

DOI: 10.1002/anie.202003614

URN: urn:nbn:de:101:1-2022061112475786379678

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

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Associated

Wübbolt, Simon
Cheong, Choon Boon
Frost, James R.
Christensen, Kirsten E.
Donohoe, Timothy J.

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Use of Iridium‐Catalyzed Transfer Vinylation for the Synthesis of Bio‐Based (bis)‐Vinyl Ethers

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Iridium-Catalyzed Synthesis of Substituted Piperazines

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Iridium-Catalyzed Enantioselective 1,6-Addition

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Iridium-Catalyzed Regio- and Enantioselective Amination

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Iridium-Catalyzed Alkylation of Allenylic Electrophiles

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A Vinyl Cyclopropane Ring Expansion and Iridium‐Catalyzed Hydrogen Borrowing Cascade

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Iridium-Catalyzed Enantioselective Cascade Allylic Etherification/(2+2) Photocycloaddition

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Use of Iridium‐Catalyzed Transfer Vinylation for the Synthesis of Bio‐Based (bis)‐Vinyl Ethers

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Palladium-Catalyzed Vinyl-Substituted Trimethylenemethane Cycloaddition

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Iridium-Catalyzed Synthesis of Substituted Piperazines

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Iridium-Catalyzed Enantioselective 1,6-Addition

Iridium-Catalyzed Enantioselective 1,6-Addition

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