Enantioselective Nickel‐Catalyzed Intramolecular Allylic Alkenylations Enabled by Reversible Alkenylnickel E/Z Isomerization

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Abstract: Enantioselective nickel‐catalyzed arylative cyclizations of substrates containing a Z‐allylic phosphate tethered to an alkyne are described. These reactions give multisubstituted chiral aza‐ and carbocycles, and are initiated by the addition of an arylboronic acid to the alkyne, followed by cyclization of the resulting alkenylnickel species onto the allylic phosphate. The reversible E/Z isomerization of the alkenylnickel species is essential for the success of the reactions.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Enantioselective Nickel‐Catalyzed Intramolecular Allylic Alkenylations Enabled by Reversible Alkenylnickel E/Z Isomerization ; volume:129 ; number:28 ; year:2017 ; pages:8328-8332 ; extent:5
Angewandte Chemie ; 129, Heft 28 (2017), 8328-8332 (gesamt 5)

Creator: Yap, Connor
Lenagh‐Snow, Gabriel M. J.
Karad, Somnath Narayan
Lewis, William
Diorazio, Louis J.
Lam, Hon Wai

DOI: 10.1002/ange.201703380

URN: urn:nbn:de:101:1-2022091406464071785322

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

Last update: 15.08.2025, 7:25 AM CEST

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Associated

Yap, Connor
Lenagh‐Snow, Gabriel M. J.
Karad, Somnath Narayan
Lewis, William
Diorazio, Louis J.
Lam, Hon Wai

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Isomerization of allylic alcohols to the ketones catalyzed by first-row transition metal pincer complexes

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Solvent-controlled E/Z isomerization vs. [2 + 2] photocycloaddition mediated by supramolecular polymerization

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Enantioselective Nickel‐Catalyzed Intramolecular Allylic Alkenylations Enabled by Reversible Alkenylnickel E/Z Isomerization

Enantioselective Nickel‐Catalyzed Intramolecular Allylic Alkenylations Enabled by Reversible Alkenylnickel E/Z Isomerization

Asymmetric Nickel-Catalyzed Intramolecular Hydroalkenylation

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Nickel-Catalyzed Intramolecular Cyclization of Dihaloalkanes

Nickel-Catalyzed Intramolecular Cyclization of Dihaloalkanes

Iron-Catalyzed Intramolecular Allylic C−H Amination

Iron-Catalyzed Intramolecular Allylic C−H Amination

Selective 1,3-Isomerization of Allylic Alcohols via Rhenium Oxo Catalysis

Selective 1,3-Isomerization of Allylic Alcohols via Rhenium Oxo Catalysis

Nickel‐Catalyzed Intramolecular Hydrosilylation of Alkynes: Embracing Conventional and Electrochemical Routes

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Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Electrochemical Nickel‐Catalyzed Selective Inter‐ and Intramolecular Arylations of Cysteine‐Containing Peptides **

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Isomerization of allylic alcohols to the ketones catalyzed by first-row transition metal pincer complexes

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Highly Selective Nickel‐Catalyzed Isomerization‐Hydroboration of Alkenes Affords Terminal Functionalization at Remote C−H Position

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Solvent-controlled E/Z isomerization vs. [2 + 2] photocycloaddition mediated by supramolecular polymerization

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