Enantioselective Catalytic (4+1)‐Cyclization of ortho ‐Hydroxy‐ para ‐Quinone Methides with Allenoates
Abstract: The first highly asymmetric catalytic synthesis of densely functionalized dihydrobenzofurans is reported, which starts from ortho‐hydroxy‐containing para‐quinone methides. The reaction relies on an unprecedented formal [4+1]‐annulation of these quinone methides with allenoates in the presence of a commercially available chiral phosphine catalyst. The chiral dihydrobenzofurans were obtained as single diastereomers in yields up to 90 % and with enantiomeric ratios up to 95:5.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Enantioselective Catalytic (4+1)‐Cyclization of ortho ‐Hydroxy‐ para ‐Quinone Methides with Allenoates ; volume:25 ; number:34 ; year:2019 ; pages:8163-8168 ; extent:6
Chemistry - a European journal ; 25, Heft 34 (2019), 8163-8168 (gesamt 6)
- Creator
- DOI
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10.1002/chem.201901784
- URN
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urn:nbn:de:101:1-2022072808175912974403
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:35 AM CEST
Data provider
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Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Zielke, Katharina
- Kováč, Ondřej
- Winter, Michael
- Pospíšil, Jiří
- Waser, Mario
Other Objects (12)
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Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst‐Controlled Cyclization of ortho ‐Quinone Methide Iminiums
Mimicking Nature: Enantioselective Cationic Polyene Cyclization
Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective (4+3)‐Cycloannulation of ortho ‐Quinone Methides and Carbonyl Ylides
Enantioselective Arylation of Enecarbamates with Quinone Imine Ketals
α-hydroxy [Alpha-hydroxy] acids in enantioselective syntheses
Mannich base-connected syntheses mediated by ortho-quinone methides
Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
Enantioselective Borylcupration/Cyclization of Alkene‐Tethered Oxime Esters
Enantioselective Borylcupration/Cyclization of Alkene‐Tethered Oxime Esters
Asymmetric Catalytic Transformations of Aza‐ ortho ‐ and Aza‐ para ‐Quinone Methides
Enantioselective cycloaddition reactions of ortho-quinone methide imines
Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst‐Controlled Cyclization of ortho ‐Quinone Methide Iminiums
Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst‐Controlled Cyclization of ortho ‐Quinone Methide Iminiums
Mimicking Nature: Enantioselective Cationic Polyene Cyclization
Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective (4+3)‐Cycloannulation of ortho ‐Quinone Methides and Carbonyl Ylides
Enantioselective Arylation of Enecarbamates with Quinone Imine Ketals
α-hydroxy [Alpha-hydroxy] acids in enantioselective syntheses
Mannich base-connected syntheses mediated by ortho-quinone methides
Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
Enantioselective Borylcupration/Cyclization of Alkene‐Tethered Oxime Esters
Enantioselective Borylcupration/Cyclization of Alkene‐Tethered Oxime Esters
Asymmetric Catalytic Transformations of Aza‐ ortho ‐ and Aza‐ para ‐Quinone Methides
Enantioselective cycloaddition reactions of ortho-quinone methide imines
Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst‐Controlled Cyclization of ortho ‐Quinone Methide Iminiums
Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst‐Controlled Cyclization of ortho ‐Quinone Methide Iminiums
Mimicking Nature: Enantioselective Cationic Polyene Cyclization
Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective (4+3)‐Cycloannulation of ortho ‐Quinone Methides and Carbonyl Ylides
Enantioselective Arylation of Enecarbamates with Quinone Imine Ketals
α-hydroxy [Alpha-hydroxy] acids in enantioselective syntheses
Mannich base-connected syntheses mediated by ortho-quinone methides
Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
Enantioselective Borylcupration/Cyclization of Alkene‐Tethered Oxime Esters
Enantioselective Borylcupration/Cyclization of Alkene‐Tethered Oxime Esters