Organoselenium-Catalyzed Enantioselective Synthesis of 2‑Oxazolidinones from Alkenes

An operationally simple method for generating enantioenriched 2-oxazolidinones from N-Boc amines and mono- or trans-disubstituted alkenes via chiral organoselenium catalysis is described. Critical to the success of the transformation was the inclusion of triisopropylsilyl chloride (TIPSCl), likely b...

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Bibliographic Details
Published in:Organic letters 2024-08, Vol.26 (31), p.6703-6708
Main Authors: Cunningham, Carter C., Panger, Jesse L., Lupi, Michela, Denmark, Scott E.
Format: Article
Language:English
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Summary:An operationally simple method for generating enantioenriched 2-oxazolidinones from N-Boc amines and mono- or trans-disubstituted alkenes via chiral organoselenium catalysis is described. Critical to the success of the transformation was the inclusion of triisopropylsilyl chloride (TIPSCl), likely because it sequestered fluoride generated by the oxidant (N-fluorocollidinium tetrafluoroborate) throughout the reaction and suppressed side reactivity. The scope of both the amine and alkene substrates was explored, generating a variety of 2-oxazolidinones in modest to high yields with high enantioselectivities.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02377