Journal of the American Chemical Society
extend to heteroatom-substituted centers and to the construc-
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tion of all-carbon quaternary centers as well. Studies in this
connection are in progress.
(11) For a mechanistic overview of Ni-catalyzed cross-coupling,
see: (a) Hu, X Chem. Sci. 2011, 2, 1867. (b) ref 2d.
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ASSOCIATED CONTENT
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136, 6534. (b) Potter, B.; Szymaniak, A. A.; Edelstein, E. K.;
Morken, J. P. J. Am. Chem. Soc. 2014, 136, 17918.
Supporting Information. Procedures, characterization and spec-
tral data. This material is available free of charge via the Internet
(13) Review: Rovis, T. in New Frontiers in Asymmetric Catalysis,
Mikami, K.; Lautens, M. Eds. Wiley, Hoboken, NJ, 2007. Selected
C-C bond forming examples: Anhydride opening (a) Shintani, R.; Fu,
G. C. Angew. Chem., Int. Ed. 2002, 41, 1057 (b) Bercot, E. A.; Rovis,
T. J. Am. Chem. Soc. 2004, 126, 10248. (c) Johnson, J. B.; Bercot, E.
A.; Williams, C. M.; Rovis, T. Angew. Chem., Int. Ed. 2007, 46,
4514. (d) Cook, M. J.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 9302.
Cyclohexadienone additions: (e) Keilitz, J.; Newman, S. G.; Lautens,
M. Org. Lett. 2013, 15, 1148. (f) He, Z.-T.; Tian, B.; Fukui, Y.;
Tong, X.; Tian, P.; Lin, G.-Q. Angew. Chem., Int. Ed. 2013, 52, 5314.
(g) Bicycle opening: Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem.
Res. 2003, 36, 48. (h) 2-Ene-1.4-diol substitutions: Trost, B. M.; van
Vranken, D. L. Chem. Rev. 1996, 96, 395. Epoxide opening: (i)
Zhao, Y.; Weix, D. J. J. Am. Chem. Soc. 2015, 137, 3237. 2- Ene-1,4-
dione addition: (j) Aikawa, K.; Okamoto, T.; Mikami, K. J. Am.
Chem. Soc. 2012, 134, 10329. Oxetane opening: (k) Mizuno, M.;
Kanai, M.; Iida, A; Tomioka, K. Tetrahedron: Asymm. 1996, 7, 2483.
(l) Mizuno, M.; Kanai, M.; Iida, A; Tomioka, K. Tetrahedron 1997,
53, 10699. (m) Suzuki coupling of symmetric ditrifaltes: Willis, M.
C.; Powell, L. H. W.; Claverie, C. K.; Watson, S. J. Angew. Chem.,
Int. Ed. 2004, 43, 1249. (n) C-H activation/coupling: Shi, B.-F.;
Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem. Int. Ed. 2008, 47,
4882.
(14) (a) Hayashi, T.; Nizuma, S.; Kamikawa, T.; Suzuki, N.; Uo-
zumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. (b) Kamikawa, T.;
Hayashi, T. Tetrahedron 1999, 55, 3455.
(15) (a) Tello-Aburto, R.; Johnson, E. M.; Valdez, C. K.; Maio, W.
A. Org. Lett. 2012, 14, 2150. (b) Tello-Aburto, R.; Newar, T. D.;
Maio, W. A. J. Org. Chem. 2012, 77, 6271.
(16) Catalytic cross-coupling of alkyl sulfonates: see (a) Terao, J.;
Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc.
2002, 124, 4222. (b) Terao, J.; Naitoh, Y.; Kuniyasu, H.; Kambe, N.
Chem. Lett. 2003, 32, 890. (c) Nagano, T.; Hayashi, T. Org. Lett.
2004, 6, 1297. (d) Terao, J.; Todo, H.; Watanabe, H.; Ikumi, A.;
Kambe, N. Angew. Chem., Int. Ed. 2004, 43, 6180. (e) Terao, J.;
Naitoh, Y.; Kuniyasu, H.; Kambe, N. Chem. Commun. 2007, 825. (f)
Singh, S. P.; Terao, J.; Kambe, N. Tetrahedron Lett. 2009, 50, 5644.
(g) Ito, S.; Fujiwara, Y.; Nakamura, E.; Nakamura, M. Org. Lett.
2009, 11, 4306. (h) Ren, P.; Stern, L.-A.; Hu, X. Angew. Chem., Int.
Ed. 2012, 51, 9110. (i) Yang, C. T.; Zhang, Z. Q.; Liang, J.; Liu, J.
H.; Lu, X. Y.; Chen, H. H.; Liu, L. J. Am. Chem. Soc. 2012, 134,
11124. (j) Iwasaki, T.; Imanishi, R.; Shimizu, R.; Kuniyasu, H.;
Terao, J.; Kambe, N. J. Org. Chem. 2014, 79, 8522.
AUTHOR INFORMATION
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Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENT
This work was supported by the NIH (GM-64451).
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