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Synthesis of Enantioenriched gem-Disubstituted 4-Imidazolidinones by Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

Sercel, Zachary P. and Sun, Alexander W. and Stoltz, Brian M. (2021) Synthesis of Enantioenriched gem-Disubstituted 4-Imidazolidinones by Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation. Organic Letters, 23 (16). pp. 6348-6351. ISSN 1523-7060. doi:10.1021/acs.orglett.1c02134. https://resolver.caltech.edu/CaltechAUTHORS:20210823-170520379

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Abstract

A variety of enantioenriched gem-disubstituted 4-imidazolidinones were prepared in up to >99% yield and 95% ee by the Pd-catalyzed decarboxylative asymmetric allylic alkylation of imidazolidinone-derived β-amidoesters. In the process of preparing these substrates, a rapid synthetic route to 4-imidazolidinone derivatives was developed, beginning from 2-thiohydantoin. The orthogonality of the benzoyl imide and tert-butyl carbamate groups used to protect these nitrogen-rich products was demonstrated, enabling potential applications in drug design.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.1c02134DOIArticle
ORCID:
AuthorORCID
Sun, Alexander W.0000-0001-6639-4469
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2021 American Chemical Society. Received: June 25, 2021; Published: August 4, 2021. The NIH-NIGMS (R01GM080269) and Caltech are thanked for financial support. Z.P.S. thanks the Rose Hills Foundation for support via a Rose Hills Foundation Graduate Fellowship and the National Science Foundation for a predoctoral fellowship. A.W.S. thanks the NIH-NIGMS for a predoctoral fellowship (Ruth L. Kirschstein Institutional National Research Service Award F30GM120836) and a UCLA-Caltech Medical Scientist Training Program Fellowship (T32GM008042). We thank Dr. Scott Virgil (Caltech) for instrumentation and helpful discussions, Dr. David VanderVelde (Caltech) for NMR expertise, and Dr. Mona Shahgoli (Caltech) for mass spectrometry assistance. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
CaltechUNSPECIFIED
Rose Hills FoundationUNSPECIFIED
NSF Graduate Research FellowshipUNSPECIFIED
NIH Predoctoral FellowshipF30GM120836
UCLA-Caltech Medical Scientist Training ProgramUNSPECIFIED
NIH Predoctoral FellowshipT32GM008042
Subject Keywords:Alcohols, Stereoselectivity, Solvents, Pharmaceuticals, Post-translational modification
Issue or Number:16
DOI:10.1021/acs.orglett.1c02134
Record Number:CaltechAUTHORS:20210823-170520379
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210823-170520379
Official Citation:Synthesis of Enantioenriched gem-Disubstituted 4-Imidazolidinones by Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation. Zachary P. Sercel, Alexander W. Sun, and Brian M. Stoltz. Organic Letters 2021 23 (16), 6348-6351; DOI: 10.1021/acs.orglett.1c02134
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:110381
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:24 Aug 2021 18:45
Last Modified:24 Aug 2021 18:45

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