Hong, Allen Y. and Krout, Michael R. and Jensen, Thomas and Bennett, Nathan B. and Harned, Andrew M. and Stoltz, Brian M. (2011) Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ-Quaternary Acylcyclopentenes. Angewandte Chemie International Edition, 50 (12). pp. 2756-2760. ISSN 1433-7851 http://resolver.caltech.edu/CaltechAUTHORS:20110329-133407762
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Contraction action! A simple protocol for the catalytic asymmetric synthesis of highly functionalized γ-quaternary acylcyclopentenes (see schematic) in up to 91 % overall yield and 92 % ee has been developed. The reaction sequence employs a palladium-catalyzed enantioselective alkylation reaction and exploits the unusual stability of β-hydroxy cycloheptanones to achieve a general and robust method for performing two-carbon ring contractions.
|Additional Information:||© 2011 Wiley. Received: December 12, 2010. Article first published online: 24 Feb 2011. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01M080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. M.R.K. acknowledges Eli Lilly for a predoctoral fellowship. T.J. acknowledges the Danish Council for Independent Research/Natural Sciences for a postdoctoral fellowship. Materia, Inc. is gratefully acknowledged for the donation of catalysts. Lawrence Henling and Dr. Michael Day are gratefully acknowledged for X-ray crystallographic structure determination. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased via an NSF CRIF:MU award to Caltech (CHE-0639094). Prof. Sarah Reisman, Dr. Scott Virgil, Dr. Christopher Henry, and Nathaniel Sherden are acknowledged for helpful discussions. Dr. David VanderVelde and Dr. Scott Ross are acknowledged for NMR assistance. The Varian 400 MR instrument used in this study was purchased via an NIH award to Caltech (NIH RR027690). Dr. Mona Shahgholi and Naseem Torian are acknowledged for high-resolution mass spectrometry assistance.|
|Subject Keywords:||aldol reaction; allylation; asymmetric catalysis; rearrangement reactions; ring contraction|
|Official Citation:||Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ-Quaternary Acylcyclopentenes (pages 2756–2760) Allen Y. Hong, Michael R. Krout, Thomas Jensen, Nathan B. Bennett, Andrew M. Harned and Brian M. Stoltz Article first published online: 24 FEB 2011 | DOI: 10.1002/anie.201007814|
|Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Ruth Sustaita|
|Deposited On:||29 Mar 2011 21:21|
|Last Modified:||29 Mar 2011 21:21|
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