Asymmetric Synthesis of α-Trifluoromethylthio-β-Amino Acids under Phase Transfer Catalysis
Entity
UAM. Departamento de Química OrgánicaPublisher
American Chemical SocietyDate
2020-01-03Citation
10.1021/acs.orglett.9b04195
Organic Letters 22.1 (2020): 219-223
ISSN
1523-7060 (print); 1523-7052 (online)DOI
10.1021/acs.orglett.9b04195Funded by
We are grateful to the Spanish Government (CTQ2015-64561-R and RTI2018-095038-B-I00), “Comunidad de Madrid” and European Structural Funds (S2018/NMT-4367). R.I.R thanks Fundación Carolina for a graduate fellowship. G.D.S and M.S. thank the University of Salerno for financial support (FARB)Project
Gobierno de España. CTQ2015-64561-R; Gobierno de España. RTI2018-095038-B-I00; Comunidad de Madrid. S2018/NMT-4367Editor's Version
https://doi.org/10.1021/acs.orglett.9b04195Subjects
Catalysts; Chemical reactions; Reaction products; Stereoselectivity; Enantioselective synthesis; QuímicaNote
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see: https://pubs.acs.org/doi/abs/10.1021/acs.orglett.9b04195Rights
© 2019 American Chemical SocietyAbstract
The first asymmetric α-trifluoromethylthiolation of 2-substituted isoxazolidin-5-ones was developed using Maruoka type N-spiro ammonium catalysts under phase-transfer conditions. The resulting products, containing a trifluoromethylthiolated quaternary chiral carbon, were obtained in moderate to good yields and up to 98:2 enantiomeric ratio. Moreover, the easy N-O bond cleavage provided access to undescribed α-trifluoromethylthio-β2,2-amino acids, with promising applications in biochemistry and medicinal chemistry.
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Google Scholar:Capaccio, Vito
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Sicignano, Marina
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Rodríguez, Ricardo I.
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Della Sala, Giorgio
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Alemán Lara, José Julián
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