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Enantioselective Synthesis of α-Secondary and α-Tertiary Piperazin-2-ones and Piperazines by Catalytic Asymmetric Allylic Alkylation

Korch, Katerina M. and Eidamshaus, Christian and Behenna, Douglas C. and Nam, Sangkil and Horne, David and Stoltz, Brian M. (2015) Enantioselective Synthesis of α-Secondary and α-Tertiary Piperazin-2-ones and Piperazines by Catalytic Asymmetric Allylic Alkylation. Angewandte Chemie International Edition, 54 (1). pp. 179-183. ISSN 1433-7851. PMCID PMC4285707. https://resolver.caltech.edu/CaltechAUTHORS:20141117-092808886

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Abstract

The asymmetric palladium-catalyzed decarboxylative allylic alkylation of differentially N-protected piperazin-2-ones allows the synthesis of a variety of highly enantioenriched tertiary piperazine-2-ones. Deprotection and reduction affords the corresponding tertiary piperazines, which can be employed for the synthesis of medicinally important analogues. The introduction of these chiral tertiary piperazines resulted in imatinib analogues which exhibited comparable antiproliferative activity to that of their corresponding imatinib counterparts.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201408609DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201408609/abstractPublisherArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201408609/suppinfoPublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4285707/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: August 27, 2014, Article first published online: 7 NOV 2014. We wish to thank the NIH-NIGMS (R01GM080269) for financial support. This material is based upon work supported by the National Science Foundation Graduate Research Fellowship under Grant No. DGE-1144469 (fellowship to K.M.K.). We also wish to thank the Deutsche Forschungsgemeinschaft (DFG postdoctoral fellowship to C.E.), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. Corey Reeves is acknowledged for providing allyl cyanoformate and for insightful discussions. Douglas Duquette is acknowledged for providing allyl 1H-imidazole-1-carboxylate reagents and for insightful discussions. Scott Virgil is acknowledged for assistance with instrumentation and insightful discussions.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
NSF Graduate Research FellowshipDGE-1144469
Deutsche Forschungsgemeinschaft (DFG)UNSPECIFIED
AmgenUNSPECIFIED
AbbottUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:allylic compounds; asymmetric catalysis; enantioselectivity; heterocycles; palladium
Issue or Number:1
PubMed Central ID:PMC4285707
Record Number:CaltechAUTHORS:20141117-092808886
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20141117-092808886
Official Citation:Korch, K. M., Eidamshaus, C., Behenna, D. C., Nam, S., Horne, D. and Stoltz, B. M. (2015), Enantioselective Synthesis of α-Secondary and α-Tertiary Piperazin-2-ones and Piperazines by Catalytic Asymmetric Allylic Alkylation. Angew. Chem. Int. Ed., 54: 179–183. doi: 10.1002/anie.201408609
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:51824
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:17 Nov 2014 21:19
Last Modified:03 Oct 2019 07:36

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