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Expanding Insight into Asymmetric Palladium-Catalyzed Allylic Alkylation of N-Heterocyclic Molecules and Cyclic Ketones

Bennett, Nathan B. and Duquette, Douglas C. and Kim, Jimin and Liu, Wen-Bo and Marziale, Alexander N. and Behenna, Douglas C. and Virgil, Scott C. and Stoltz, Brian M. (2013) Expanding Insight into Asymmetric Palladium-Catalyzed Allylic Alkylation of N-Heterocyclic Molecules and Cyclic Ketones. Chemistry: a European Journal, 19 (14). pp. 4414-4418. ISSN 0947-6539. PMCID PMC3815597. https://resolver.caltech.edu/CaltechAUTHORS:20130501-072844784

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Abstract

Eeny, meeny, miny … enaminones! Lactams and imides have been shown to consistently provide enantioselectivities substantially higher than other substrate classes previously investigated in the palladium-catalyzed asymmetric decarboxylative allylic alkylation. Several new substrates have been designed to probe the contributions of electronic, steric, and stereoelectronic factors that distinguish the lactam/imide series as superior alkylation substrates (see scheme). These studies culminated in marked improvements on carbocyclic allylic alkylation substrates.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/chem.201300030DOIArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815597/PubMed CentralArticle
ORCID:
AuthorORCID
Liu, Wen-Bo0000-0003-2687-557X
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2013 Wiley-VCH Verlag GmbH & Co. Issue published online: 20 Mar 2013. Article first published online: 27 Feb 2013. Manuscript Received: 12 Nov 2012. The authors thank NIH-NIGMS (R01 M080269-01), Roche, Abbott Laboratories, Amgen, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for awards and financial support. D.C.D. thanks the National Science Foundation for financial support (Predoctoral Research Fellowship, No. DGE-1144469). W.-B.L. thanks the Shanghai Institute of Organic Chemistry for financial support (SIOC Postdoctoral Fellowship). A.N.M. is grateful for a fellowship by the Deutsche Akademie der Naturforscher Leopoldina. Profs. Sarah Reisman and Theodor Agapie are acknowledged for helpful discussions and suggestions. Dr. David VanderVelde and Dr. Scott Ross are acknowledged for NMR assistance. Dr. Mona Shahgoli and Naseem Torian are acknowledged for High-Resolution Mass Spectrometry assistance.
Funders:
Funding AgencyGrant Number
NIHR01 M080269-01
RocheUNSPECIFIED
Abbott LaboratoriesUNSPECIFIED
AmgenUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
NSF Predoctoral FellowshipDGE-1144469
Shangai Institute of Organic ChemistryUNSPECIFIED
Deutsche Akademie der Naturforscher LeopoldinaUNSPECIFIED
Subject Keywords:allylation; asymmetric catalysis; heterocyclic compounds; high-throughput screening; palladium
Issue or Number:14
PubMed Central ID:PMC3815597
Record Number:CaltechAUTHORS:20130501-072844784
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130501-072844784
Official Citation:Bennett, N. B., Duquette, D. C., Kim, J., Liu, W.-B., Marziale, A. N., Behenna, D. C., Virgil, S. C. and Stoltz, B. M. (2013), Expanding Insight into Asymmetric Palladium-Catalyzed Allylic Alkylation of N-Heterocyclic Molecules and Cyclic Ketones. Chem. Eur. J., 19: 4414–4418. doi: 10.1002/chem.201300030
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:38193
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:01 May 2013 15:01
Last Modified:22 Apr 2020 19:59

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