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Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones

Duquette, Douglas C. and Cusumano, Alexander Q. and Lefoulon, Louise and Moore, Jared T. and Stoltz, Brian M. (2020) Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones. Organic Letters, 22 (13). pp. 4966-4969. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20200622-104137176

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Abstract

Herein, we report the palladium-catalyzed decarboxylative asymmetric allylic alkylation of α-enaminones. In addition to serving as valuable synthetic building blocks, we exploit the α-enaminone scaffold and its derivatives as probes to highlight structural and electronic factors that govern enantioselectivity in this asymmetric alkylation reaction. Utilizing the (S)-t-BuPHOX ligand in a variety of nonpolar solvents, the alkylated products are obtained in up to 99% yield and 99% enantiomeric excess.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.0c01441DOIArticle
ORCID:
AuthorORCID
Cusumano, Alexander Q.0000-0002-2914-2008
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2020 American Chemical Society. Received: April 25, 2020; Published: June 16, 2020. We thank the NIH-NIGMS (R01GM080269), and the NSF (predoctoral research fellowship to D.C.D., No. DGE-1144469) for financial support. Research reported in this publication was supported by the NIH-NIGMS under Award Number F32GM116304 (postdoctoral fellowship to J. T. Moore). We further thank Dr. Scott C. Virgil (Caltech) for assistance with chiral-SFC separation and insightful discussion. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
NSF Graduate Research FellowshipDGE-1144469
NIH Postdoctoral FellowshipF32GM116304
Issue or Number:13
Record Number:CaltechAUTHORS:20200622-104137176
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200622-104137176
Official Citation:Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones. Douglas C. Duquette, Alexander Q. Cusumano, Louise Lefoulon, Jared T. Moore, and Brian M. Stoltz. Organic Letters 2020 22 (13), 4966-4969; DOI: 10.1021/acs.orglett.0c01441
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:103952
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:23 Jun 2020 14:30
Last Modified:07 Jul 2020 23:16

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