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

doi:10.1021/acs.orglett.9b02192

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

Org Lett. 2019 Aug 16;21(16):6305-6309. doi: 10.1021/acs.orglett.9b02192. Epub 2019 Jul 29.

Authors

Amandeep Brar¹, Daniel K Unruh¹, Natalie Ling¹, Clemens Krempner¹

Affiliation

¹ Department of Chemistry & Biochemistry , Texas Tech University , Box 41061, Lubbock , Texas 79409-1061 , United States.

PMID: 31356091
DOI: 10.1021/acs.orglett.9b02192

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.