Organic Letters
Letter
18O atom. These facts confirm that the hydroxy group is not
from water. At the same time, the similar 18O-labeling
experiments were also conducted with olefinic imide 1h. The
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In conclusion, we have developed a highly regio-, enantio-,
and diastereoselective oxytrifluoromethylthiolation of aliphatic
internal alkenes to synthesize CF3S-substituted 1,3-amino
alcohol and 1,3-diol derivatives in a formally intermolecular
fashion by chiral selenide catalysis. This method is also
effective for the stereoselective halogenation of internal alkenes
and the conversion of internal alkynes. Importantly, this work
contains a strategy that alkenes can be regioselectively
functionalized by neighboring imide or ester group to deliver
a functional group.
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ASSOCIATED CONTENT
* Supporting Information
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The Supporting Information is available free of charge on the
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Experimental details, characterization data, HPLC traces,
and NMR spectra of new compounds (PDF)
Accession Codes
tallographic data for this paper. These data can be obtained
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Author Contributions
†J.X. and Y.Z. contributed equally to this work.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank Sun Yat-Sen University, the “One Thousand Youth
Talents” Program of China, the National Natural Science
Foundation of China (Grant No. 21772239), and the Natural
Science Foundation of Guangdong Province (Grant No.
2014A030312018) for financial support.
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Chem. Lett. 1998, 8, 487. (c) Benedetti, F.; Norbedo, S. Chem.
Commun. 2001, 203. (d) Lee, H.-S.; Kang, S. H. Synlett 2004, 1673.
For molecules containing 1,3-diol moieties, see: (e) Rychnovsky, S. D.
Chem. Rev. 1995, 95, 2021. (f) Koskinen, A. M. P.; Karisalmi, K.
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