Organic Letters
Letter
Hu, X. H.; Chen, S.; Hu, X. P. Org. Lett. 2014, 16, 588. (j) Zhang, D.
Y.; Zhu, F. L.; Wang, Y. H.; Hu, X. H.; Chen, S.; Hou, C. J.; Hu, X. P.
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8192.
rivatives in moderate to excellent yields with excellent
enantioselectivities. In sharp contrast to previously reported
intermolecular annulation reactions of copper−allenylidenes
from ethynyl benzoxazinanone working as a quaternary
synthon, ethynyl benzoxazinanones act as a C3 synthon in
the current annulation reaction and three carbon atoms of
propargyl moiety were fused into the heterocyclic framework.
(3) Nishibayashi, Y.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem.
Soc. 2002, 124, 7900.
ASSOCIATED CONTENT
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(4) Pan, Y.-M.; Zhao, S.-Y.; Ji, W.-H.; Zhan, Z.-P. J. Comb. Chem.
2009, 11, 103.
S
* Supporting Information
The Supporting Information is available free of charge on the
(5) Lu, Q.; Cembellin, S.; Gressies, S.; Singha, S.; Daniliuc, C. G.;
Glorius, F. Angew. Chem., Int. Ed. 2018, 57, 1399.
(6) For selected examples, see: (a) Zhang, C.; Hu, X. H.; Wang, Y.
H.; Zheng, Z.; Xu, J.; Hu, X. P. J. Am. Chem. Soc. 2012, 134, 9585.
(b) Zhu, F. L.; Wang, Y. H.; Zhang, D. Y.; Xu, J.; Hu, X. P. Angew.
Chem., Int. Ed. 2014, 53, 10223. (c) Li, Q.; Hou, C.-J.; Hui, Y.-Z.; Liu,
Y.-J.; Yang, R.-F.; Hu, X.-P. RSC Adv. 2015, 5, 85879. (d) Zhang, D.-
Y.; Shao, L.; Xu, J.; Hu, X.-P. ACS Catal. 2015, 5, 5026. (e) Liu, Z. T.;
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(7) Wang, Q.; Li, T. R.; Lu, L. Q.; Li, M. M.; Zhang, K.; Xiao, W. J. J.
Am. Chem. Soc. 2016, 138, 8360.
(8) Li, T. R.; Cheng, B. Y.; Wang, Y. N.; Zhang, M. M.; Lu, L. Q.;
Xiao, W. J. Angew. Chem., Int. Ed. 2016, 55, 12422.
(9) Li, T. R.; Lu, L. Q.; Wang, Y. N.; Wang, B. C.; Xiao, W. J. Org.
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(10) Li, T. R.; Zhang, M. M.; Wang, B. C.; Lu, L. Q.; Xiao, W. J. Org.
Lett. 2018, 20, 3237.
(11) Wang, B. C.; Wang, Y. N.; Zhang, M. M.; Xiao, W. J.; Lu, L. Q.
Chem. Commun. 2018, 54, 3154.
(12) Song, J.; Zhang, Z. J.; Gong, L. Z. Angew. Chem., Int. Ed. 2017,
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(13) Shao, W.; You, S. L. Chem. - Eur. J. 2017, 23, 12489.
(14) Lu, X.; Ge, L.; Cheng, C.; Chen, J.; Cao, W.; Wu, X. Chem. -
Eur. J. 2017, 23, 7689.
Experimental procedures, characterization data, HPLC
analysis dada, NMR spectra and X-ray crystallographic
Accession Codes
CCDC 1844053 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Authors
ORCID
Notes
The authors declare no competing financial interest.
(15) Chen, H.; Lu, X.; Xia, X.; Zhu, Q.; Song, Y.; Chen, J.; Cao, W.;
Wu, X. Org. Lett. 2018, 20, 1760.
(16) Zhang, Y. C.; Zhang, Z. J.; Fan, L. F.; Song, J. Org. Lett. 2018,
20, 2792.
ACKNOWLEDGMENTS
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This work is supported by the NSFC (21372256 and
21572264) and the Program for Changjiang Scholars and
Innovative Research Team Project IRT1042.
(17) Ji, D.; Wang, C.; Sun, J. Org. Lett. 2018, 20, 3710.
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