Light‐Driven Enantioselective Organocatalytic β‐Benzylation of Enals
Abstract: A photochemical organocatalytic strategy for the direct enantioselective β‐benzylation of α,β‐unsaturated aldehydes is reported. The chemistry capitalizes upon the light‐triggered enolization of 2‐alkyl‐benzophenones to afford hydroxy‐o‐quinodinomethanes. These fleeting intermediates are stereoselectively intercepted by chiral iminium ions, transiently formed upon condensation of a secondary amine catalyst with enals. Density functional theory (DFT) studies provided an explanation for why the reaction proceeds through an unconventional Michael‐type addition manifold, instead of a classical cycloaddition mechanism and subsequent ring‐opening.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Light‐Driven Enantioselective Organocatalytic β‐Benzylation of Enals ; volume:56 ; number:12 ; year:2017 ; pages:3304-3308 ; extent:5
Angewandte Chemie / International edition. International edition ; 56, Heft 12 (2017), 3304-3308 (gesamt 5)
- Urheber
- DOI
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10.1002/anie.201612159
- URN
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urn:nbn:de:101:1-2022092107021660533277
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:37 MESZ
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Beteiligte
- Dell'Amico, Luca
- Fernández‐Alvarez, Victor M.
- Maseras, Feliu
- Melchiorre, Paolo
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