Organic Letters
Letter
T.; Miura, M. Angew. Chem., Int. Ed. 2012, 51, 3642. (g) Matsuda, N.;
Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2012, 51,
11827. (h) Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013,
15, 172. (i) Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem.
Soc. 2013, 135, 4934. (j) Sakae, R.; Hirano, K.; Satoh, T.; Miura, M.
Chem. Lett. 2013, 42, 1128.
(16) For recent examples of copper-catalyzed intra- and intermo-
lecular hydroamination of alkenes, see: (a) Taylor, J. G.; Whittall, N.;
Hii, K. K. Org. Lett. 2006, 8, 3561. (b) Munro-Leighton, C.; Delp, S.
A.; Blue, E. D.; Gunnoe, T. B. Organometallics 2007, 26, 1483.
(c) Munro-Leighton, C.; Delp, S. A.; Alsop, N. M.; Blue, E. D.;
Gunnoe, T. B. Chem. Commun. 2008, 111. (d) Ohmiya, H.; Morita, T.;
Sawamura, M. Org. Lett. 2009, 11, 2145. (e) Turnpenny, B. W.;
Hyman, K. L.; Chemler, S. R. Organometallics 2012, 31, 7819.
(6) Reviews: (a) Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947.
(b) Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 21, 4505.
(c) Ciganek, E. Org. React. 2009, 72, 1. (d) Barker, T. J.; Jarvo, E. R.
Synthesis 2011, 3954. Recent examples: (e) Berman, A. M.; Johnson, J.
S. J. Am. Chem. Soc. 2004, 126, 5680. (f) Campbell, M. J.; Johnson, J. S.
Org. Lett. 2007, 9, 1521. (g) Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc.
2008, 130, 6918. (h) He, C.; Chen, C.; Cheng, J.; Liu, C.; Liu, W.; Li,
Q.; Lei, A. Angew. Chem., Int. Ed. 2008, 47, 6414. (i) Barker, T. J.;
Jarvo, E. R. J. Am. Chem. Soc. 2009, 131, 15598. (j) Hatakeyama, T.;
Yoshimoto, Y.; Ghorai, S. K.; Nakamura, M. Org. Lett. 2010, 12, 1516.
(k) Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. J. Am. Chem.
Soc. 2012, 134, 6571. (l) Grohmann, C.; Wang, H.; Glorius, F. Org.
Lett. 2012, 14, 656. (m) Xiao, Q.; Tian, L.; Tan, R.; Xia, Y.; Qiu, D.;
Zhang, Y.; Wang, J. Org. Lett. 2012, 14, 4230. (n) Mlynarski, S. N.;
Karns, A. S.; Morken, J. P. J. Am. Chem. Soc. 2012, 134, 16449.
(o) Zhu, C.; Li, G.; Ess, D. H.; Falck, J. R.; Kurti, L. J. Am. Chem. Soc.
̈
2012, 134, 18253. (p) Miura, T.; Morimoto, M.; Murakami, M. Org.
Lett. 2012, 14, 5214. (q) Qian, X.; Yu, Z.; Auffrant, A.; Gosmini, C.
Chem.Eur. J. 2013, 19, 6225. (r) Dong, Z.; Dong, G. J. Am. Chem.
Soc. 2013, 135, 18350. (s) Matsubara, T.; Asako, S.; Ilies, L.;
Nakamura, E. J. Am. Chem. Soc. 2014, 136, 646. (t) Shang, M.; Zeng,
S.-H.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. Org. Lett. 2013, 15, 5286.
(u) Wu, K.; Fan, Z.; Xue, Y.; Yao, Q.; Zhang, A. Org. Lett. 2014, 16, 42.
(7) Review: Deutsch, C.; Krause, N.; Lipshutz, B. H. Chem. Rev.
2008, 108, 2916.
(8) (a) Lillo, V.; Fructos, M. R.; Ramírez, J.; Braga, A. A. C.; Maseras,
F.; Díaz-Requejo, M. M.; Per
2007, 13, 2614. (b) Noh, D.; Chea, H.; Ju, J.; Yun, J. Angew. Chem., Int.
́
ez, P. J.; Fernan
́
dez, E. Chem.Eur. J.
Ed. 2009, 48, 6062.
(9) The carbon-bridged norbornenes underwent the enantioselective
hydroamination; see ref 2a,b,n.
(10) (a) Smith, E. C. R.; Riley, T. N.; Borne, R. F.; Waters, I. W. J.
Med. Chem. 1987, 30, 1105. (b) Kouvarakis, A.; Thermos, K.; Hieble,
J. P.; Katerinopoulos, H. E. Eur. J. Med. Chem. 1993, 28, 251.
̌
(c) Hre
Neyts, J.; Kaniakova,
1286.
̌
babecky, H.; Dejmek, M.; Drací
̌
nsky, M.; Sal
́
a, M.; Leyssen, P.;
̌
M.; Krusek, J.; Nencka, R. Tetrahedron 2012, 68,
̊
́
́
́
(11) Accounts and reviews: (a) Lautens, M.; Fagnou, K.; Hiebert, S.
Acc. Chem. Res. 2003, 36, 48. (b) Rayabarapu, D. K.; Cheng, C.-H. Acc.
Chem. Res. 2007, 40, 971. (c) Bournaud, C.; Chung, F.; Luna, A. P.;
Pasco, M.; Errasti, G.; Lecourt, T.; Micouin, L. Synthesis 2009, 869.
Selected examples of the ring-opening amination: (d) Lautens, M.;
Fagnou, K.; Rovis, T. J. Am. Chem. Soc. 2000, 122, 5650. (e) Lautens,
M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125, 14884. (f) Yang,
D.; Ping, Hu.; Long, Y.; Wu, Y.; Zeng, H.; Wang, H.; Zuo, X. Beilstein
J. Org. Chem. 2009, 5, 53. (g) Webster, R.; Boing, C.; Lautens, M. J.
̈
Am. Chem. Soc. 2009, 131, 444.
(12) (a) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G.
Tetrahedron Lett. 1998, 39, 1313. (b) Cadierno, V.; García-Garrido, S.
E.; Gimeno, J.; Nebra, N. Chem. Commun. 2005, 4086. (c) Wang, J.-Y.;
Wang, D.-X.; Zheng, Q.-Y.; Huang, Z.-T.; Wang, M.-X. J. Org. Chem.
2007, 72, 2040.
(13) (a) Noack, M.; Gottlich, R. Chem. Commun. 2002, 536. Also
̈
see: (b) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3,
2709. (c) Tsuritani, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2003,
68, 3246.
(14) See the Supporting Information for detailed solvent effects on
yields and enantiomeric ratios.
(15) Under the standard conditions, the reaction of 2,5-dihydrofuran
or norbornadiene with 2a did not proceed at all. Thus, the ring strain
associated with the bicyclic framework could be critical to promote the
reaction, and heteroatoms at the bridged position and the benzene
fusion on the norbornene backbone further increased the reactivity.
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dx.doi.org/10.1021/ol5003219 | Org. Lett. 2014, 16, 1498−1501