Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium (I) Migration

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Abstract: Alkenyl‐to‐allyl 1,4‐rhodium (I) migration enables the generation of nucleophilic allylrhodium (I) species by remote C−H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing a 1,3‐enyne tethered to a ketone, to give products containing three contiguous stereocenters. The products can be obtained in high enantioselectivities using a chiral sulfur‐alkene ligand.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium (I) Migration ; volume:56 ; number:25 ; year:2017 ; pages:7227-7232 ; extent:6
Angewandte Chemie / International edition. International edition ; 56, Heft 25 (2017), 7227-7232 (gesamt 6)

Creator: Partridge, Benjamin M.
Callingham, Michael
Lewis, William
Lam, Hon Wai

DOI: 10.1002/anie.201703155

URN: urn:nbn:de:101:1-2022091307343240609990

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

Partridge, Benjamin M.
Callingham, Michael
Lewis, William
Lam, Hon Wai

Other Objects (12)

Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium (I) Migration

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Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium (I) Migration

Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium (I) Migration

Enantioselective Addition of Allyl Bromides to Ketones

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Enantioselective Allylation and Halocyclization of Allyl Hydrazides and Allyl Oximes for the Synthesis of Enantioenriched Pyrazolidines and Isoxazolidines

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Nickel-catalyzed direct stereoselective α-allylation of ketones with non-conjugated dienes

Nickel-catalyzed direct stereoselective α-allylation of ketones with non-conjugated dienes

Copper hydride catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes

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Catalytic Photoinduced Intramolecular Decarboxylative and Desulfonylative sp 3 Allylation Enabled by Sulfinate Salts

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Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium (I) Migration

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Enantioselective Allylation and Halocyclization of Allyl Hydrazides and Allyl Oximes for the Synthesis of Enantioenriched Pyrazolidines and Isoxazolidines

Nickel-catalyzed direct stereoselective α-allylation of ketones with non-conjugated dienes

Nickel-catalyzed direct stereoselective α-allylation of ketones with non-conjugated dienes

Copper hydride catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes

Copper hydride catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes

Hegedus Indole Synthesis: Intramolecular Nucleopalladation of ortho-Allyl Aryl Nucleophiles

Hegedus Indole Synthesis: Intramolecular Nucleopalladation of ortho-Allyl Aryl Nucleophiles

Catalytic Photoinduced Intramolecular Decarboxylative and Desulfonylative sp 3 Allylation Enabled by Sulfinate Salts

Catalytic Photoinduced Intramolecular Decarboxylative and Desulfonylative sp 3 Allylation Enabled by Sulfinate Salts

Catalytic Photoinduced Intramolecular Decarboxylative and Desulfonylative sp 3 Allylation Enabled by Sulfinate Salts

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Directed C−H Allylation of Aromatic Carboxamides with Allyl Aryl Ethers under Cp*Co (III)‐Catalysis

Directed C−H Allylation of Aromatic Carboxamides with Allyl Aryl Ethers under Cp*Co (III)‐Catalysis

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C−C Bond Formation by Dual Pyrrolidine and Nickel Catalysis: Allylation of Ketones by Allylic Alcohols

Ruthenium (II)-Catalyzed C–H Allylation of N,N-Dialkylthiobenzamides with Allyl Methyl Carbonate by Sulfur Coordination

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Synthesis of Macrocyclic Amides Using Manganese (III)- Based Intramolecular Cyclization of N-(ω-Alkenyl)-3- oxobutanamides

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