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Published August 20, 2021 | Accepted Version + Supplemental Material
Journal Article Open

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

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.

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.

Attached Files

Accepted Version - nihms-1745715.pdf

Supplemental Material - ol1c02134_si_001.pdf

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Additional details

Created:
August 20, 2023
Modified:
October 23, 2023