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ChemComm
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COMMUNICATION
Journal Name
reaction, the cis/trans selectivity could be controlled by A1,3
Fujimoto, Y. Funakoshi and M. MurakaDmOi,I:A10n.g10e3w9./CC7hCeCm02.,5I2n1tA.
Ed., 2015, 54, 9967; (j) D. J. Lee, D. Ko, E. J. Yoo, Angew.
Chem., Int. Ed., 2015, 54, 13715; (k) T. Miura, T. Nakamuro, S.
Miyakawa and M. Murakami, Angew. Chem., Int. Ed., 2016,
55, 8732; (l) D. Yadagiri, A. C. S. Reddy and P. Anbarasan,
strain and gauche strain (Scheme 4B). In intermediate
3,
because of the A1,3 strain between [Rh] and R group,
conformation 3-1 was favored than 3-2, and after addition of
the oxygen in carbonyl to C=Rh double bond, 10-trans, rather
than 10-cis, should be generated easier. An antiperiplanar
relationship between C-Rh bond and the leaving C-O bond in
11 led to the formation of kinetic controlled intermediate 5-
Chem. Sci., 2016, 7, 5934; (m) W. Zhou, M. Zhang, H. Li and
W. Chen, Org. Lett., 2017, 19, 10. For related publications of
our group, see: (n) R.-Q. Ran, J. He, S.-D. Xiu, K.-B. Wang and
C.-Y. Li, Org. Lett., 2014, 16, 3704; (o) R.-Q. Ran, S.-D. Xiu and
C.-Y. Li, Org. Lett., 2014, 16, 6394; (p) W.-B. Zhang, S.-D. Xiu
trans
.
In conclusion, a convenient protocol for the generation of
1,2-dihydropyridines was achieved by the rhodium-catalyzed
tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole.
The crucial intermediate penta-2,4-dien-1-imine was obtained
by 1,2-migration of an ester group with excellent
chemoselectivity. The ready access to the substrates, the mild
reaction conditions and the versatility of the dihydropyridines
should enhance the synthetic potential of this transformation.
This work was generously supported by the National
Natural Science Foundation of China (21372204), the Program
for Innovative Research Team of Zhejiang Sci-Tech University
(13060052-Y) and Zhejiang Sci-Tech University 521 project.
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4 | J. Name., 2012, 00, 1-3
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