Reeves, Corey M. and Eidamshaus, Christian and Kim, Jimin and Stoltz, Brian M. (2013) Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation. Angewandte Chemie International Edition, 52 (26). pp. 6718-6721. ISSN 1433-7851. PMCID PMC3817853. https://resolver.caltech.edu/CaltechAUTHORS:20130809-133957166
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Abstract
No strain, no gain! The first transition metal-catalyzed enantioselective α-alkylation of cyclobutanones is reported. This method employs palladium catalysis and an electron-deficient PHOX-type ligand to afford all-carbon α-quaternary cyclobutanones in good to excellent yields and enantioselectivities (see scheme).
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Additional Information: | © 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: March 4, 2013; Revised: April 17, 2013; Published online: May 17, 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. | ||||||||||||||
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Subject Keywords: | allylic alkylation; asymmetric catalysis; cyclobutanone; palladium; quaternary center | ||||||||||||||
Issue or Number: | 26 | ||||||||||||||
PubMed Central ID: | PMC3817853 | ||||||||||||||
Record Number: | CaltechAUTHORS:20130809-133957166 | ||||||||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20130809-133957166 | ||||||||||||||
Official Citation: | Reeves, C. M., Eidamshaus, C., Kim, J. and Stoltz, B. M. (2013), Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation . Angew. Chem. Int. Ed., 52: 6718–6721. doi: 10.1002/anie.201301815 | ||||||||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||
ID Code: | 39845 | ||||||||||||||
Collection: | CaltechAUTHORS | ||||||||||||||
Deposited By: | Tony Diaz | ||||||||||||||
Deposited On: | 09 Aug 2013 20:57 | ||||||||||||||
Last Modified: | 21 Apr 2020 23:58 |
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