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

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).


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201301815 DOIArticle
http://dx.doi.org/10.1002/anie.201305706DOIErrata
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817853/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
NIHR01GM080269-01
Deutsche Forschungsgemeinschaft (DFG)UNSPECIFIED
AmgenUNSPECIFIED
AbbottUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
CaltechUNSPECIFIED
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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