Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic (2,3)‐Meisenheimer Rearrangements
Abstract: Chiral acyclic tertiary allylic alcohols are very important synthetic building blocks, but their enantioselective synthesis is often challenging. A major limitation in catalytic asymmetric 1,2‐addition approaches to ketones is the enantioface differentiation by steric distinction of both ketone residues. Herein we report the development of a catalytic asymmetric Meisenheimer rearrangement to overcome this problem, as it proceeds in a stereospecific manner. This allows for high enantioselectivity also for the formation of products in which the residues at the generated tetrasubstituted stereocenter display a similar steric demand. Low catalyst loadings were found to be sufficient and the reaction conditions were mild enough to tolerate even highly reactive functional groups, such as an enolizable aldehyde, a primary tosylate, or an epoxide. Our investigations suggest an intramolecular rearrangement pathway.
- 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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Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic (2,3)‐Meisenheimer Rearrangements ; volume:59 ; number:27 ; year:2020 ; pages:10944-10948 ; extent:5
Angewandte Chemie / International edition. International edition ; 59, Heft 27 (2020), 10944-10948 (gesamt 5)
- Urheber
- DOI
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10.1002/anie.202001725
- URN
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urn:nbn:de:101:1-2022061409110495856201
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:39 MESZ
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Beteiligte
- Yu, Xin
- Wannenmacher, Nick
- Peters, René
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