Journal of the American Chemical Society
Communication
Int. Ed. 2015, 54, 6531. (d) Shen, C.; Liu, R.; Fan, R.; Li, Y.; Xu, T.; Gao,
J.; Jia, Y. J. Am. Chem. Soc. 2015, 137, 4936.
ASSOCIATED CONTENT
Supporting Information
■
*
S
(
9) (a) Pinto, A.; Jia, Y.; Neuville, L.; Zhu, J. Chem. - Eur. J. 2007, 13,
61. (b) For alternative cyanoamidation of alkenes, see: Yasui, Y.;
Kamisaki, H.; Takemoto, Y. Org. Lett. 2008, 10, 3303.
10) For examples of using asymmetric Heck reaction, see:
a) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am.
9
(
Crystallographic data for (R)-6 (CIF)
Crystallographic data for (R)-9aa (CIF)
Experimental procedures, spectroscopic data (PDF)
(
Chem. Soc. 1998, 120, 6477. (b) Ashimori, A.; Bachand, B.; Calter, M. A.;
Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120,
6
488. (c) Oestreich, M.; Dennison, P. R.; Kodanko, T. J.; Overman, L. E.
Angew. Chem., Int. Ed. 2001, 40, 1439.
11) For alternative enantioselective synthesis of oxindoles/indolines
via formation of the C −C bond, see: (a) Lee, S.; Hartwig, J. F. J. Org.
AUTHOR INFORMATION
(
3
3a
Chem. 2001, 66, 3402. (b) Glorius, F.; Altenhoff, G.; Goddard, R.;
Lehmann, C. Chem. Commun. 2002, 2704. (c) Kundig, E. P.; Seidel, T.
M.; Jia, Y.-X.; Bernardinelli, G. Angew. Chem., Int. Ed. 2007, 46, 8484.
d) Nakanishi, M.; Katayev, D.; Besnard, C.; Kundig, E. P. Angew. Chem.,
Notes
̈
The authors declare no competing financial interest.
(
̈
Int. Ed. 2011, 50, 7438. (e) Anas, S.; Cordi, A.; Kagan, H. B. Chem.
Commun. 2011, 47, 11483. (f) Saget, T.; Lemouzy, S.; Cramer, N.
Angew. Chem., Int. Ed. 2012, 51, 2238. (g) Katayev, D.; Nakanishi, M.;
ACKNOWLEDGMENTS
We thank EPFL, the Swiss National Science Foundation
SNSF), and the Swiss National Centres of Competence in
Research (NCCR-Chemical Biology) for financial support. We
are grateful to Dr. Rosario Scopelliti for performing X-ray
structural analysis.
■
(
̈ ̈
Burgi, T.; Kundig, E. P. Chem. Sci. 2012, 3, 1422. (h) Martin, N.; Pierre,
C.; Davi, M.; Jazzar, R.; Baudoin, O. Chem. - Eur. J. 2012, 18, 4480.
(i) Wu, L.; Falivene, L.; Drinkel, E.; Grant, S.; Linden, A.; Cavallo, L.;
Dorta, R. Angew. Chem., Int. Ed. 2012, 51, 2870. For reviews on
enantioselective CH-functionalization, see: (j) Giri, R.; Shi, B.-F.; Engle,
K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242.
REFERENCES
■
(
12) Takano, S.; Ogasawara, K. In The Alkaloids, Vol. 36; Brossi, A.,
Ed.; Academic Press: San Diego, 1989; p 225.
13) (a) Steven, A.; Overman, L. E. Angew. Chem., Int. Ed. 2007, 46,
488. (b) Schmidt, M. A.; Movassaghi, M. Synlett 2008, 2008, 313.
14) Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997,
997, 1338.
15) Castagnetti, E.; Schlosser, M. Chem. - Eur. J. 2002, 8, 799.
(
1) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738.
2) Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989,
4, 5846.
3) (a) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
b) Shibasaki, M.; Vogl, E. M.; Ohshima, T. Adv. Synth. Catal. 2004, 346,
533. (c) McCartney, D. M.; Guiry, P. Chem. Soc. Rev. 2011, 40, 5122.
d) Mei, T.-S.; Patel, H. H.; Sigman, M. S. Nature 2014, 508, 340. (e)
For a monograph, see: The Mizoroki−Heck Reaction; Oestreich, M., Ed.;
Wiley: New York, 2009.
4) (a) Kagechika, K.; Shibasaki, M. J. Org. Chem. 1991, 56, 4093.
b) Kagechika, K.; Ohshima, T.; Shibasaki, M. Tetrahedron 1993, 49,
773. (c) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.;
Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108. (d) Overman, L. E.;
Rosen, M. D. Angew. Chem., Int. Ed. 2000, 39, 4596. (e) Overman, L. E.;
Rosen, M. Tetrahedron 2010, 66, 6514.
(
(
5
(
1
5
(
(
1
(
(
3
(16) Pentafluorobenzene can be used to trap the transient C −Pd
sp
intermediate under racemic conditions. We thank one of the referees for
suggesting this experiment. Other heterocycles such as 2-chlorothio-
phene and oxazoles are also suitable substrates. However, further
optimization is needed for the enantioselective version. Pyrimidine,
benzoimidazole, and indole failed to participate in this domino process.
(
(
1
(
17) (a) Ruck, R. T.; Huffman, M. A.; Kim, M. M.; Shevlin, M.; Kandur,
W. V.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 47, 4711.
b) Satyanarayana, G.; Maichle-Mossmer, C.; Maier, M. E. Chem.
(
̈
(
̈
5) For selected examples, see: (a) Grigg, R.; Koppen, I.; Rasparini, M.;
Commun. 2009, 1571. (c) Hu, Y.; Yu, C.; Ren, D.; Hu, Q.; Zhang, L.;
Cheng, D. Angew. Chem., Int. Ed. 2009, 48, 5448. (d) Piou, T.; Neuville,
L.; Zhu, J. Org. Lett. 2012, 14, 3760. (e) Piou, T.; Neuville, L.; Zhu, J.
Angew. Chem., Int. Ed. 2012, 51, 11561.
Sridharan, V. Chem. Commun. 2001, 964. (b) Lu, Z.; Hu, C.; Guo, J.; Li,
J.; Cui, Y.; Jia, Y. Org. Lett. 2010, 12, 480. (c) Jaegli, S.; Dufour, J.; Wei,
H.; Piou, T.; Duan, X.; Vors, J. P.; Neuville, L.; Zhu, J. Org. Lett. 2010, 12,
4
498. (d) Jaegli, S.; Erb, W.; Retailleau, P.; Vors, J. P.; Neuville, L.; Zhu,
(
18) C−H Activation. Topics in Current Chemistry, Vol. 292; Yu, J.-Q.,
Shi, Z. J., Eds.; Springer: Berlin, 2010.
19) (a) Karig, G.; Moon, M.-T.; Thasana, N.; Gallagher, T. Org. Lett.
002, 4, 3115. (b) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock,
J. Chem. - Eur. J. 2010, 16, 5863. (e) Jaegli, S.; Vors, J. P.; Neuville, L.;
Zhu, J. Tetrahedron 2010, 66, 8911. (f) Wu, T.; Mu, X.; Liu, G. Angew.
Chem., Int. Ed. 2011, 50, 12578. (g) Mu, X.; Wu, T.; Wang, H.; Guo, Y.;
Liu, G. J. Am. Chem. Soc. 2012, 134, 878. (h) Liu, X.; Ma, X.; Huang, Y.;
Gu, Z. Org. Lett. 2013, 15, 4814. (i) Liu, Z.; Xia, Y.; Zhou, S.; Wang, L.;
Zhang, Y.; Wang, J. Org. Lett. 2013, 15, 5032. (j) Fan, J.; Wei, W.; Zhou,
M.; Song, R.; Li, J.-H. Angew. Chem., Int. Ed. 2014, 53, 6650.
(
2
R. C. J. Am. Chem. Soc. 2004, 126, 7460. (c) Piou, T.; Bunescu, A.; Wang,
Q.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2013, 52, 12385.
(20) A trace amount of water present in the reaction media served as a
proton source.
(
k) Vachhani, D. D.; Butani, H. H.; Sharma, N.; Bhoya, U. C.; Shah,
(
(
21) We thank one of the referees for suggesting this experiment.
22) (a) Rice, R. G.; Kohn, E. J. J. Am. Chem. Soc. 1955, 77, 4052.
A. K.; Van der Eycken, E. V. Chem. Commun. 2015, 51, 14862. For
recent reviews, see: (l) Klein, J. E. M. N.; Taylor, R. J. K. Eur. J. Org.
Chem. 2011, 2011, 6821. (m) Tsui, G. C.; Lautens, M. C−H Activations
in Domino Processes. In Domino Reactions; Tietze, L. F., Ed.; Wiley-
VCH: Weinheim, 2014; p 67.
(
b) Ainsworth, C. J. Am. Chem. Soc. 1956, 78, 1635. (c) Rice, R. G.;
Kohn, E. J.; Daasch, L. W. J. Org. Chem. 1958, 23, 1352.
23) (a) Ainsworth, C. J. Am. Chem. Soc. 1954, 76, 5774. (b) Hinman,
R. L. J. Am. Chem. Soc. 1956, 78, 1645.
24) Kobayashi, Y.; Kamisaki, H.; Takeda, H.; Yasui, Y.; Yanada, R.;
Takemoto, Y. Tetrahedron 2007, 63, 2978.
25) For reviews, see: (a) Millemaggi, A.; Taylor, R. J. K. Eur. J. Org.
(
(
6) (a) Rene, O.; Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4560.
(
2
Only methacrylamides (R = Me, cf. Scheme 1c) was used in this study.
For reviews on direct cross-coupling, see: (b) Ackermann, L.; Vicente,
R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792. (c) Zhao, D.; You,
J.; Hu, C. Chem. - Eur. J. 2011, 17, 5466. (d) Bugaut, X.; Glorius, F.
Angew. Chem., Int. Ed. 2011, 50, 7479.
(
Chem. 2010, 2010, 4527. (b) Musmade, D. S.; Pattan, S. R.; Manjunath,
S. Y. Int. J. Pharma. Chem. 2015, 5, 11.
(
7) Clavier, H.; Pellissier, H. Adv. Synth. Catal. 2012, 354, 3347.
(
8) (a) Diaz, P.; Gendre, F.; Stella, L.; Charpentier, B. Tetrahedron
1
2
998, 54, 4579. (b) Minatti, M.; Zheng, X.; Buchwald, S. L. J. Org. Chem.
007, 72, 9253. (c) Yue, G.; Lei, K.; Hirao, H.; Zhou, J. Angew. Chem.,
1
6031
J. Am. Chem. Soc. 2015, 137, 16028−16031