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Modular Bis(oxazoline) Ligands for Palladium Catalyzed Allylic Alkylation: Unprecedented Conformational Behaviour of a Bis(oxazoline) Palladium 3-1,3-Diphenylallyl Complex

2002; Wiley; Volume: 8; Issue: 18 Linguagem: Inglês

10.1002/1521-3765(20020916)8

1521-3765

Miquel À. Pericàs, Cristina Puigjaner, Antoni Riéra, Anton Vidal‐Ferran, Montserrat Gómez, Francisco Jiménez, Guillermo Muller, Mercè Rocamora,

Oxidative Organic Chemistry Reactions

Chemistry – A European JournalVolume 8, Issue 18 p. 4164-4178 Full Paper Modular Bis(oxazoline) Ligands for Palladium Catalyzed Allylic Alkylation: Unprecedented Conformational Behaviour of a Bis(oxazoline) Palladium η3-1,3-Diphenylallyl Complex Miquel Angel Pericàs Prof., Miquel Angel Pericàs Prof. [email protected] Departament de Química Orgànica Universitat de Barcelona Parc Científic de Barcelona, Josep Samitier 1-5 08028 Barcelona (Spain) Fax: (+34) 93-4037095Search for more papers by this authorCristina Puigjaner Dr., Cristina Puigjaner Dr. Departament de Química Orgànica Universitat de Barcelona Parc Científic de Barcelona, Josep Samitier 1-5 08028 Barcelona (Spain) Fax: (+34) 93-4037095Search for more papers by this authorAntoni Riera Dr., Antoni Riera Dr. Departament de Química Orgànica Universitat de Barcelona Parc Científic de Barcelona, Josep Samitier 1-5 08028 Barcelona (Spain) Fax: (+34) 93-4037095Search for more papers by this authorAnton Vidal-Ferran Dr., Anton Vidal-Ferran Dr. Departament de Química Orgànica Universitat de Barcelona Parc Científic de Barcelona, Josep Samitier 1-5 08028 Barcelona (Spain) Fax: (+34) 93-4037095Search for more papers by this authorMontserrat Gómez Dr., Montserrat Gómez Dr. Departament de Química Inorgànica Universitat de Barcelona Martí i Franquès 1-11, 08028 Barcelona (Spain) Fax: (+34) 93-4907725Search for more papers by this authorFrancisco Jiménez Sr., Francisco Jiménez Sr. Departament de Química Inorgànica Universitat de Barcelona Martí i Franquès 1-11, 08028 Barcelona (Spain) Fax: (+34) 93-4907725Search for more papers by this authorGuillermo Muller Prof., Guillermo Muller Prof. [email protected] Departament de Química Inorgànica Universitat de Barcelona Martí i Franquès 1-11, 08028 Barcelona (Spain) Fax: (+34) 93-4907725Search for more papers by this authorMercè Rocamora Dr., Mercè Rocamora Dr. Departament de Química Inorgànica Universitat de Barcelona Martí i Franquès 1-11, 08028 Barcelona (Spain) Fax: (+34) 93-4907725Search for more papers by this author Miquel Angel Pericàs Prof., Miquel Angel Pericàs Prof. [email protected] Departament de Química Orgànica Universitat de Barcelona Parc Científic de Barcelona, Josep Samitier 1-5 08028 Barcelona (Spain) Fax: (+34) 93-4037095Search for more papers by this authorCristina Puigjaner Dr., Cristina Puigjaner Dr. Departament de Química Orgànica Universitat de Barcelona Parc Científic de Barcelona, Josep Samitier 1-5 08028 Barcelona (Spain) Fax: (+34) 93-4037095Search for more papers by this authorAntoni Riera Dr., Antoni Riera Dr. Departament de Química Orgànica Universitat de Barcelona Parc Científic de Barcelona, Josep Samitier 1-5 08028 Barcelona (Spain) Fax: (+34) 93-4037095Search for more papers by this authorAnton Vidal-Ferran Dr., Anton Vidal-Ferran Dr. Departament de Química Orgànica Universitat de Barcelona Parc Científic de Barcelona, Josep Samitier 1-5 08028 Barcelona (Spain) Fax: (+34) 93-4037095Search for more papers by this authorMontserrat Gómez Dr., Montserrat Gómez Dr. Departament de Química Inorgànica Universitat de Barcelona Martí i Franquès 1-11, 08028 Barcelona (Spain) Fax: (+34) 93-4907725Search for more papers by this authorFrancisco Jiménez Sr., Francisco Jiménez Sr. Departament de Química Inorgànica Universitat de Barcelona Martí i Franquès 1-11, 08028 Barcelona (Spain) Fax: (+34) 93-4907725Search for more papers by this authorGuillermo Muller Prof., Guillermo Muller Prof. [email protected] Departament de Química Inorgànica Universitat de Barcelona Martí i Franquès 1-11, 08028 Barcelona (Spain) Fax: (+34) 93-4907725Search for more papers by this authorMercè Rocamora Dr., Mercè Rocamora Dr. Departament de Química Inorgànica Universitat de Barcelona Martí i Franquès 1-11, 08028 Barcelona (Spain) Fax: (+34) 93-4907725Search for more papers by this author First published: 16 September 2002 https://doi.org/10.1002/1521-3765(20020916)8:18 3.0.CO;2-GCitations: 77Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Graphical Abstract Highly enantioselective asymmetric allylic alkylation can be obtained with allylpalladium complexes derived from modular enantiopure bis(oxazolines) (up to 96 %). Both the R and Ar residues were optimized with regards to the catalytic activity in the AAA reaction (see scheme). Abstract New families of enantiopure bis(oxazolines) with 4,5-trans (5 a–g) or 4,5-cis (6 c) stereochemistry at the individual rings have been prepared in high yield. Their η3-allyl palladium complexes (8 a–g, 9 c and 10) have been used as catalytic precursors in allylic alkylation reactions with excellent enantioselectivities (up to 96 %) for the trans oxazoline derivatives, while Pd/6 c system was inactive. NMR studies on palladium η3-1,3-diphenylallyl intermediates (11 a, c and e) showed the presence of syn/syn- and syn/anti-allyl isomers in solution; this resembles the first example of η3-η1-η3 isomerism in Pd allylic complexes containing bis(oxazolines) derived from malonic acid. Citing Literature Volume8, Issue18September 16, 2002Pages 4164-4178 RelatedInformation