BPh3-Catalyzed [2+3] Cycloaddition of Ph3PCCO with Aldonitrones: Access to 5-Isoxazolidinones with Exocyclic Phosphonium Ylide Moieties

Amandeep Brar, Daniel K. Unruh, Natalie Ling, Clemens Krempner

Research output: Contribution to journalArticle

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Abstract

A method for the generation of 5-isoxazolidinones with exocyclic phosphonium ylide functionalities via [2+3] cycloaddition of Ph3PCCO and aldonitrones has been developed and applied in the synthesis of 4-alkylidene-5-isoxazolidinones via Wittig olefination. The reaction proceeds by BPh3 catalysis under mild conditions and with a broad substrate scope. A reaction pathway involving the activation of the aldonitrone via interactions with the Lewis acid BPh3 is proposed.

Original languageEnglish
Pages (from-to)6305-6309
Number of pages5
JournalOrganic Letters
Volume21
Issue number16
DOIs
StatePublished - Aug 16 2019

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