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Organic Letters

Organic Letters

IF: 4.9
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Organoselenium-Catalyzed Enantioselective Synthesis of 2-Oxazolidinones from Alkenes.

Published:9 August 2024 DOI: 10.1021/acs.orglett.4c02377 PMID: 39082836
Carter C Cunningham,?Jesse L Panger,?Michela Lupi,?Scott E Denmark

Abstract

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.

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Related products
Procduct Name CAS Molecular Formula Supplier Price
Triisopropylsilyl chloride 13154-24-0 C9H21ClSi 556 suppliers $8.00-$1649.00
3-Bromo-N-methyl-N-boc-propylamine 828272-19-1 C9H18BrNO2 42 suppliers Inquiry
1-Benzyl-3-butylimidazolium tetrafluoroborate 642443-67-2 C14H19BF4N2 1 suppliers Inquiry

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