Chiral Brønsted Acid‐Catalyzed Enantioselective α‐Amidoalkylation Reactions: A Joint Experimental and Predictive Study
Abstract: Enamides with a free NH group have been evaluated as nucleophiles in chiral Brønsted acid‐catalyzed enantioselective α‐amidoalkylation reactions of bicyclic hydroxylactams for the generation of quaternary stereocenters. A quantitative structure–reactivity relationship (QSRR) method has been developed to find a useful tool to rationalize the enantioselectivity in this and related processes and to orient the catalyst choice. This correlative perturbation theory (PT)‐QSRR approach has been used to predict the effect of the structure of the substrate, nucleophile, and catalyst, as well as the experimental conditions, on the enantioselectivity. In this way, trends to improve the experimental results could be found without engaging in a long‐term empirical investigation.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Chiral Brønsted Acid‐Catalyzed Enantioselective α‐Amidoalkylation Reactions: A Joint Experimental and Predictive Study ; volume:5 ; number:6 ; year:2016 ; pages:540-549 ; extent:10
ChemistryOpen ; 5, Heft 6 (2016), 540-549 (gesamt 10)
- Creator
-
Aranzamendi, Eider
Arrasate, Sonia
Sotomayor, Nuria
González‐Díaz, Humberto
Lete, Esther
- DOI
-
10.1002/open.201600120
- URN
-
urn:nbn:de:101:1-2022112107154665105927
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
15.08.2025, 7:30 AM CEST
Data provider
This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Aranzamendi, Eider
- Arrasate, Sonia
- Sotomayor, Nuria
- González‐Díaz, Humberto
- Lete, Esther
Other Objects (12)
Brønsted Acid Catalyzed Enantioselective Indole Aza-Claisen Rearrangement
Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement
Brønsted acid catalyzed enantioselective addition of hydrazones to 3-indolylmethanols
Brønsted‐Acid Catalyzed Diastereo‐ and Enantioselective Synthesis of Spiroisoindolinones from Enamides
Enantioselective Rhodium-Catalyzed Synthesis of Axially Chiral Biaryls
Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones
Desymmetrization of Oxabenzonorbornadienes through Brønsted Acid‐Catalyzed Enantioselective (3+2) Cycloaddition with Hydrazones
Brønsted Base‐Catalyzed Enantioselective α‐Functionalization of Carbonyl Compounds Involving π‐Extended Enolates
Innovative strategies for the enantioselective synthesis of nitrogen-containing heterocycles by chiral Brønsted acid catalysis & nickel catalyzed decarbonylative sp2-sp3 coupling
Chiral Quaternary Ammonium Salt‐Catalyzed Enantioselective Addition Reactions of Hydantoins
Copper-Catalyzed Enantioselective [1,3]-Rearrangement to Chiral Propargylic Amines
Brønsted Acid Catalyzed Enantioselective Indole Aza-Claisen Rearrangement
Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement
Brønsted acid catalyzed enantioselective addition of hydrazones to 3-indolylmethanols
Brønsted‐Acid Catalyzed Diastereo‐ and Enantioselective Synthesis of Spiroisoindolinones from Enamides
Enantioselective Rhodium-Catalyzed Synthesis of Axially Chiral Biaryls
Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones
Desymmetrization of Oxabenzonorbornadienes through Brønsted Acid‐Catalyzed Enantioselective (3+2) Cycloaddition with Hydrazones
Brønsted Base‐Catalyzed Enantioselective α‐Functionalization of Carbonyl Compounds Involving π‐Extended Enolates
Innovative strategies for the enantioselective synthesis of nitrogen-containing heterocycles by chiral Brønsted acid catalysis & nickel catalyzed decarbonylative sp2-sp3 coupling
Chiral Quaternary Ammonium Salt‐Catalyzed Enantioselective Addition Reactions of Hydantoins
Copper-Catalyzed Enantioselective [1,3]-Rearrangement to Chiral Propargylic Amines
Brønsted Acid Catalyzed Enantioselective Indole Aza-Claisen Rearrangement
Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement
Brønsted acid catalyzed enantioselective addition of hydrazones to 3-indolylmethanols
Brønsted‐Acid Catalyzed Diastereo‐ and Enantioselective Synthesis of Spiroisoindolinones from Enamides
Enantioselective Rhodium-Catalyzed Synthesis of Axially Chiral Biaryls
Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones
Desymmetrization of Oxabenzonorbornadienes through Brønsted Acid‐Catalyzed Enantioselective (3+2) Cycloaddition with Hydrazones
Brønsted Base‐Catalyzed Enantioselective α‐Functionalization of Carbonyl Compounds Involving π‐Extended Enolates
Innovative strategies for the enantioselective synthesis of nitrogen-containing heterocycles by chiral Brønsted acid catalysis & nickel catalyzed decarbonylative sp2-sp3 coupling
Chiral Quaternary Ammonium Salt‐Catalyzed Enantioselective Addition Reactions of Hydantoins