Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Aryloxindoles with Allylidene Dipivalate: A Useful Enol Pivalate Product†
Corresponding Author
Prof. Barry M. Trost
Department of Chemistry, Stanford University, Stanford CA 94305-4401 (USA) http://www.stanford.edu/group/bmtrost
Department of Chemistry, Stanford University, Stanford CA 94305-4401 (USA) http://www.stanford.edu/group/bmtrost===Search for more papers by this authorJames T. Masters
Department of Chemistry, Stanford University, Stanford CA 94305-4401 (USA) http://www.stanford.edu/group/bmtrost
Search for more papers by this authorDr. Aaron C. Burns
Department of Chemistry, Stanford University, Stanford CA 94305-4401 (USA) http://www.stanford.edu/group/bmtrost
Search for more papers by this authorCorresponding Author
Prof. Barry M. Trost
Department of Chemistry, Stanford University, Stanford CA 94305-4401 (USA) http://www.stanford.edu/group/bmtrost
Department of Chemistry, Stanford University, Stanford CA 94305-4401 (USA) http://www.stanford.edu/group/bmtrost===Search for more papers by this authorJames T. Masters
Department of Chemistry, Stanford University, Stanford CA 94305-4401 (USA) http://www.stanford.edu/group/bmtrost
Search for more papers by this authorDr. Aaron C. Burns
Department of Chemistry, Stanford University, Stanford CA 94305-4401 (USA) http://www.stanford.edu/group/bmtrost
Search for more papers by this authorWe thank the National Institutes of Health (R01GM033049) and the National Science Foundation for their generous support of our programs. J.T.M. is supported by an Abbott Laboratories Stanford Graduate Fellowship. We also thank Johnson-Matthey for their generous gift of palladium salts.
Graphical Abstract
Dreifach A: Die katalytische asymmetrische allylische Alkylierung (AAA) von 3-Aryloxindolen mit Allylidendipivalat wird beschrieben. Die Reaktion liefert stabile, präparativ nützliche Enolpivalate in hohen Ausbeuten und mit exzellenter Regio- und Enantioselektivität. Eine Bandbreite von Substraten wird toleriert, darunter ungeschützte und 3-Heteroaryl-Nucleophile.
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References
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