DOI: 10.1039/C9GC01030K
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Journal Name
Green Chemistry
ARTICLE
Chem. Int. Ed., 2011, 50, 8629; (e) T. A. Wenderski, M. A. Marsini
and T. R. R. Pettus, Org. Lett., 2011, 13, 118.
Conclusions
3
For recent examples, see: (a) G. Albano, M. Morelli and L. A.
Aronica, Eur. J. Org. Chem., 2017, 3473; (b) Y. Hu, Z. Shen and H.
Huang, ACS Catal., 2016, 6, 6785; (c) R. Akula and P. J. Guiry, Org.
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6046; (f) A. Rioz-Martínez, G. de Gonzalo, D. E. Torres Pazmiño,
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2012, 44, 175; For recent selected examples, see: (c) M. C. Blanco
Jaimes, V. Weingand, F. Rominger and A. S. K. Hashmi, Chem. –
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Döpp, M. Ackermann, J. De Buck Becker, M. Rudolph, C. Scholz
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(f) F. M. Istrate and F. Gagosz, Beilstein J. Org. Chem., 2011, 7,
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11863.
In summary, we have developed a metal-free intramolecular
alkoxylation-initiated cascade cyclization of allyl ether-tethered
ynamides. A variety of highly functionalized 3-isochromanones
can be easily constructed by this simple method under mild
conditions. Moreover, this asymmetric cyclization is also
realized via
a stereocontrolled [3,3] rearrangement by
employing a traceless chiral directing group. In addition, an
unexpected [1,3] O-to-C rearrangement is observed in case of
the ynamide substrate bearing phenyl-substituted alkene, which
is distinctively different from the related gold catalysis and
constitutes a rare example of Brønsted acid-catalyzed [1,3] O-
to-C rearrangement.
4
Acknowledgements
We are grateful for the financial support from the National
Natural Science Foundation of China (21622204 and
21772161), the President Research Funds from Xiamen
University (20720180036), PCSIRT, NFFTBS (J1310024), and
Science & Technology Cooperation Program of Xiamen
(3502Z20183015). We also thank Mr Zanbin Wei from Xiamen
University for assistance with X-ray crystallographic analysis.
5
For
Au-catalyzed
intermolecular
hydroalkoxylation/Claisen
rearrangement, see: (a) J. Li, L. Lin, B. Hu, P. Zhou, T. Huang, X.
Liu and X. Feng, Angew. Chem. Int. Ed., 2017, 56, 885; (b) N. Li,
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