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ChemComm
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COMMUNICATION
Journal Name
In conclusion, we developed the first bifunctional organic-
base catalyzed 1,4-conjugate addition to in situ generated N-o-
QMs with good to excellent enantioselectivities (up to 94% ee)
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DOI: 10.1039/C8CC09382B
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at H O/DCM interface. Being complementary in scope to
existing chiral phosphoric acids-catalyzed reactions of N-o-
QMs, this reaction provides a uniquely valuable method for
the enantioselective synthesis of ortho-amino substituted
benzyl mercaptans. Experimental results indicate that water is
crucial for achieving the high reactivity and stereoselectivity.
This study paves a new route for the asymmetric reactions
involving N-o-QMs. Future studies are underway to extend this
strategy to other nucleophiles in our laboratory.
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3, 2247; (g) L. Caruana, M. Mondatori, V. Corti, S. Morales,
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Acknowledgements
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X.-M Feng, Chem. Commun., 2015, 51, 3835; (i) Y. Huang and
T. Hayashi, J. Am. Chem. Soc., 2015, 137, 7556; (j) S. Saha and
C. Schneider, Chem. Eur. J., 2015, 21, 2348; (k) Z.-B Wang, F.
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This work is financially supported by the National Natural
Science Foundation of China (21871254, 21532006, 21472187)
and DICP (DICP ZZBS201602).
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