Dynamic Kinetic Resolution Allows Control of Remote Stereochemistry in Asymmetric Hydrogen Borrowing Alkylation

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Abstract: A catalytic asymmetric method for the synthesis of γ‐substituted ketones via hydrogen borrowing alkylation of both racemic linear precursors and 1,5‐diols is described. The base mediated racemization of an intermediate cyclohexenone to facilitates a dynamic kinetic resolution, affording highly enantioenriched cyclohexanes in excellent yields, which could be further functionalized by removal of the Ph* group. DFT modelling revealed the mode of enantioinduction to be a stepwise process comprising of a hydride transfer and a coordination change to a π‐allylic enolate complex with the iridium catalyst.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Dynamic Kinetic Resolution Allows Control of Remote Stereochemistry in Asymmetric Hydrogen Borrowing Alkylation ; day:27 ; month:02 ; year:2025 ; extent:7
Angewandte Chemie / International edition. International edition ; (27.02.2025) (gesamt 7)

Creator: Cheang, Daniella M. J.
Crompton, Jessica L.
Amer, Mostafa M.
Battiti, Francisco
Skjelstad, Bastian Bjerkem
Christensen, Kirsten E.
Barton, Peter
Duarte, Fernanda
Donohoe, Timothy J.

DOI: 10.1002/anie.202424959

URN: urn:nbn:de:101:1-2502271433138.529118465054

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

Last update: 15.08.2025, 7:29 AM CEST

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Associated

Cheang, Daniella M. J.
Crompton, Jessica L.
Amer, Mostafa M.
Battiti, Francisco
Skjelstad, Bastian Bjerkem
Christensen, Kirsten E.
Barton, Peter
Duarte, Fernanda
Donohoe, Timothy J.

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