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Chemical Science
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Journal Name
ARTICLE
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Scheme 4. Preliminary results for a catalytic asymmetric version.
Our preliminary results for a catalytic asymmetric version of this
reaction is shown in Scheme 4. When chiral PCCP catalyst22 was
o
added in step 3 and the reaction temperature lowered to -20 C, α-
amino ketone 3ba was obtained in 67% yield and 50% ee, which
indicate the feasibility to develop a chiral Brønsted acid catalyzed
reaction to prepare enantioenriched α-amino ketones directly from
alkynes.
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Conclusions
In conclusion, we have developed a general procedure for the
synthesis of α-heterosubstituted ketones through sulfur mediated
difunctionalization of internal alkynes. A variety of α-substituted
ketones could be prepared by using nitrogen, oxygen, sulfur and
halogen nucleophiles. Applications for the synthesis of
heterocycles and derivatization of natural product are also
realized. We are currently exploring the catalytic asymmetric
version of this reaction, and those results will be reported in due
course.
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Conflicts of interest
There are no conflicts to declare.
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DOI: 10.1021/acs.joc.9b00136.
Acknowledgements
This research was supported in part by National Natural Science
Foundation of China (21402005, 21572017) and the
Fundamental Research Funds for the Central Universities (XK-
1802-6, 12060093063).
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Notes and references
1. Product Class 6: α-Heterosubstituted Ketones, in Science of
Synthesis, ed. J. Cossy, Georg Thieme Verlag, Stuttgart, 2005, vol.
26.
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