Catalytic Asymmetric Synthesis of Cyclohexanes by Hydrogen Borrowing Annulations

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Abstract: Hydrogen borrowing catalysis serves as a powerful alternative to enolate alkylation, enabling the direct coupling of ketones with unactivated alcohols. However, to date, methods that enable control over the absolute stereochemical outcome of such a process have remained elusive. Here we report a catalytic asymmetric method for the synthesis of enantioenriched cyclohexanes from 1,5‐diols via hydrogen borrowing catalysis. This reaction is mediated by the addition of a chiral iridium (I) complex, which is able to impart high levels of enantioselectivity upon the process. A series of enantioenriched cyclohexanes have been prepared and the mode of enantioinduction has been probed by a combination of experimental and DFT studies.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Catalytic Asymmetric Synthesis of Cyclohexanes by Hydrogen Borrowing Annulations ; volume:58 ; number:36 ; year:2019 ; pages:12558-12562 ; extent:5
Angewandte Chemie / International edition. International edition ; 58, Heft 36 (2019), 12558-12562 (gesamt 5)

Creator: Armstrong, Roly J.
Akhtar, Wasim M.
Young, Tom A.
Duarte, Fernanda
Donohoe, Timothy J.

DOI: 10.1002/anie.201907514

URN: urn:nbn:de:101:1-2022080608153018260466

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

Last update: 15.08.2025, 7:28 AM CEST

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Associated

Armstrong, Roly J.
Akhtar, Wasim M.
Young, Tom A.
Duarte, Fernanda
Donohoe, Timothy J.

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