Synthesis of Unprotected Spirocyclic β‑Prolines and β‑Homoprolines by Rh-Catalyzed C–H Insertion

A series of unprotected spirocyclic β-prolines and β-homoprolines are prepared by Rh-catalyzed C–H insertion. The key intermediate, a Rh nitrenoid, is generated by the N–O bond cleavage of a substituted isoxazolidin-5-one. The reaction proceeds on a gram scale with a catalyst loading of as little as...

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Bibliographic Details
Published in:Organic letters 2019-12, Vol.21 (23), p.9296-9299
Main Authors: Espinosa, Miguel, Noda, Hidetoshi, Shibasaki, Masakatsu
Format: Article
Language:English
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Summary:A series of unprotected spirocyclic β-prolines and β-homoprolines are prepared by Rh-catalyzed C–H insertion. The key intermediate, a Rh nitrenoid, is generated by the N–O bond cleavage of a substituted isoxazolidin-5-one. The reaction proceeds on a gram scale with a catalyst loading of as little as 0.1 mol %, affording spirocyclic β-amino acids that are otherwise difficult to obtain. The building blocks prepared in this work will likely find applications in medicinal chemistry.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03198