Organic Letters
Letter
D.-F.; Zhang, X.-M.; Xu, X.-Y.; Yuan, W.-C. J. Org. Chem. 2015, 80,
12668.
spirocyclization process more difficult to occur. As a result,
product (R)-2p is formed in a more favored way.
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In summary, we have disclosed an unprecedented cascade
cross-coupling reaction involving the sequential formation of a
C−O bond and a C−C bond catalyzed by a flexible chiral
iodoarene of C2-symmetry and resulting in the asymmetric
synthesis of the biologically important spirofurooxindole
skeleton.15 This protocol provides a convenient pathway to
access optically active spirofurooxindoles with excellent
enantioselectivity. Further investigation of the applications of
this methodology is in progress in our laboratory.
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ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
Experimental procedures and compound characterization
Crystallographic data for 2a (CIF)
Crystallographic data for (R)-2b (CIF)
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We acknowledge the National Natural Science Foundation of
China (21472136) and the Tianjin Research Program of
Application Foundation and Advanced Technology
(15JCZDJC32900) for financial support.
(10) (a) Wu, H.; He, Y.-P.; Xu, L.; Zhang, D.-Y.; Gong, L.-Z. Angew.
Chem., Int. Ed. 2014, 53, 3466. (b) Zhang, D.-Y.; Xu, L.; Wu, H.;
Gong, L.-Z. Chem. - Eur. J. 2015, 21, 10314.
(11) (a) Volp, K. A.; Harned, A. M. Chem. Commun. 2013, 49, 3001.
(b) Murray, S. J.; Ibrahim, H. Chem. Commun. 2015, 51, 2376.
(12) Wang, J.; Yuan, Y.; Xiong, R.; Zhang-Negrerie, D.; Du, Y.; Zhao,
K. Org. Lett. 2012, 14, 2210.
(13) Sreenithya, A.; Sunoj, R. B. Org. Lett. 2014, 16, 6224.
(14) Liu, L.; Zhang, T.; Yang, Y.-F.; Zhang-Negrerie, D.; Zhang, X.;
Du, Y.; Wu, Y.-D.; Zhao, K. J. Org. Chem. 2016, 81, 4058.
(15) We also replaced the aniline moiety with a phenol and examined
the spirolactonization of the analogous ester substrate. Unfortunately,
no desired spirolactone product was obtained under our present
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