Organic Letters
Letter
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In summary, we have developed a new method for the
synthesis of β,γ-unsaturated indanones and tetralones featuring
an α-quaternary center by reaction of alkenylboronic acids with
N-tosylhydrazones tethered to a benzonitrile. In the domino
reaction the incorporation of the alkenyl group and the
cyclization reaction occur in a single step.
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Cabal, M.-P.; Valdes, C. Org. Lett. 2017, 19, 4086.
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ASSOCIATED CONTENT
* Supporting Information
(7) Xia, Y.; Wang, J. Chem. Soc. Rev. 2017, 46, 2306.
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(8) Some recent methods for the synthesis of β,γ-unsaturated
ketones: (a) Bao, M.; Lu, W.; Cai, Y.; Qiu, L.; Xu, X. J. Org. Chem.
2017, 82, 13386. (b) Wu, Y.; Fu, W. C.; Chiang, C.-W.; Choy, P. Y.;
Kwong, F. Y.; Lei, A. Chem. Commun. 2017, 53, 952. (c) Grigalunas,
M.; Ankner, T.; Norrby, P.-O.; Wiest, O.; Helquist, P. J. Am. Chem.
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Ivanova, E. V.; Ushakov, I. A. J. Org. Chem. 2012, 77, 6880 and
references cited therein .
S
The Supporting Information is available free of charge on the
Experimental procedures, compound characterization
data, and NMR spectra for the compounds described;
computational molecular modeling studies (PDF)
(9) (a) Charrier, C.; Bertrand, P.; Gesson, J.-P.; Roche, J. Bioorg.
Med. Chem. Lett. 2006, 16, 5339. (b) Sheridan, H.; Walsh, J. J.;
Cogan, C.; Jordan, M.; McCabe, T.; Passante, E.; Frankish, N. H.
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L.; Tirunagaru, V. G.; Kumar, S. ACS Med. Chem. Lett. 2018, 9, 103.
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F.; Goeke, A. Angew. Chem., Int. Ed. 2012, 51, 5647. (b) Martin-
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2010, 12, 4082. (c) Chang, B.; Su, Y.; Huang, D.; Wang, K.-H.;
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(d) Demuth, M.; Mikhail, G. Synthesis 1989, 1989, 145.
AUTHOR INFORMATION
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Corresponding Author
ORCID
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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Financial support of this work by Ministerio de Economıa y
Competitividad (MINECO) of Spain: Grant CTQ2016-
76794-P (AEI/FEDER, UE). An FPI predoctoral fellowship
(MINECO) to M. Paraja and an FPU predoctoral fellowship
(MECD) to M. Plaza are gratefully acknowledged. L.
Florentino thanks Principado de Asturias for a Marie Curie
(11) (a) Huang, J.; Bunel, E.; Faul, M. M. Org. Lett. 2007, 9, 4343.
(b) Chieffi, A.; Kamikawa, K.; Ahman, J.; Fox, J. M.; Buchwald, S. L.
Org. Lett. 2001, 3, 1897.
(12) Medina, J. M.; Moreno, J.; Racine, S.; Du, S.; Garg, N. K.
Angew. Chem., Int. Ed. 2017, 56, 6567.
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− Cların cofund postdoctoral fellowship (ref: PA-18-ACB17-
(13) (a) Shi, Y.; Gao, S. Tetrahedron 2016, 72, 1717. (b) Cao, Z.;
Zhu, H.; Meng, X.; Tian, L.; Chen, G.; Sun, X.; You, J. J. Org. Chem.
2016, 81, 12401 and references cited therein .
20).
(14) The stereochemical assignments were carried out by 2D-NMR
and selective NOE experiments (see SI for a detailed discussion).
(15) Taber, D. F.; Guo, P. J. Org. Chem. 2008, 73, 9479.
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