Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation

Authors

  • Corey M. Reeves,

    1. The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
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  • Christian Eidamshaus,

    1. The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
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  • Jimin Kim,

    1. The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
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  • Prof. Brian M. Stoltz

    Corresponding author
    1. The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
    • The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
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Errata

This article is corrected by:

  1. Errata: Berichtigung: Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation Volume 125, Issue 33, 8651, Article first published online: 8 August 2013

  • The authors wish to thank NIH-NIGMS (R01GM080269-01), Deutsche Forschungsgemeinschaft (DFG postdoctoral fellowship to C.E.), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. Materia, Inc. is gratefully acknowledged for the donation of catalysts. Dr. Mona Shahgholi and Naseem Torian are acknowledged for high-resolution mass spectrometry assistance. Jonny Gordon is acknowledged for insightful discussions. Robert Craig is gratefully acknowledged for providing compound L3 and for insightful discussion.

Abstract

original image

„Spannende“ Synthese: Die erste übergangsmetallkatalysierte α-Alkylierung von Cyclobutanonen wird beschrieben. Die Methode setzt auf eine Palladiumkatalyse mit einem elektronenarmen PHOX-Liganden und liefert α-quartäre Cyclobutanone in guten bis sehr guten Ausbeuten und Enantioselektivitäten (siehe Schema).

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