Organic Letters
Letter
Z.-J.; Vors, J.-P.; Gesing, E. R. F.; Bolm, C. Green Chem. 2011, 13, 42−
45. (d) Guillou, S.; Bonhomme, F. J.; Chahine, D. B.; Nesme, O.;
Janin, Y. L. Tetrahedron 2010, 66, 2654−2663.
(10) (a) Chen, J.; Pang, Q.; Sun, Y.; Li, X. J. Org. Chem. 2011, 76,
3523−3526. (b) Chu, J.-H.; Lin, P.-S.; Lee, Y.-M.; Shen, W.-T.; Wu,
M.-J. Chem. - Eur. J. 2011, 17, 13613−13620. (c) Chen, J.; Song, G.;
Pan, C.-L.; Li, X. Org. Lett. 2010, 12, 5426−5429.
(11) (a) Cheng, G.; Zeng, X.; Shen, J.; Wang, X.; Cui, X. Angew.
Chem., Int. Ed. 2013, 52, 13265−8. (b) Yang, X.; Cheng, G.; Shen, J.;
Kuai; Cui, X. Org. Chem. Front. 2015, 2, 366−368. (c) Wang, X.;
Cheng, G.; Cui, X. Chem. Commun. 2014, 50, 652−654. (d) Cheng,
G.; Cui, X. Org. Lett. 2013, 15, 1480−1483. (e) Shen, J.; Cheng, G.;
Cui, X. Chem. Commun. 2013, 49, 10641−10643.
(12) (a) Martins, M. A. P.; Rossatto, M.; Frizzo, C. P.; Scapin, E.;
Buriol, L.; Zanatta, N.; Bonacorso, H. G. Tetrahedron Lett. 2013, 54,
847−849. (b) Harschneck, T.; Kirsch, S. F. J. Org. Chem. 2011, 76,
2145−2156. (c) Fananas, F. J.; Arto, T.; Mendoza, A.; Rodriguez, F.
Org. Lett. 2011, 13, 4184−4187. (d) Cacchi, S.; Fabrizi, G.; Filisti, E.
Org. Lett. 2008, 10, 2629−2632.
REFERENCES
■
(1) Michael, J. P. Nat. Prod. Rep. 2005, 22, 627−646.
(2) (a) Kang, S.; Song, B.; Wu, J.; He, M.; Hu, D.; Jin, L.; Zeng, S.;
Xue, W.; Yang, S. Eur. J. Med. Chem. 2013, 67, 14−18. (b) Wang, X.;
Wu, Y. J. J. Econ. Entomol. 2012, 105, 1019−1023.
(3) (a) Balbi, A.; Anzaldi, M.; Maccio, C.; Aiello, C.; Mazzei, M.;
Gangemi, R.; Castagnola, P.; Miele, M.; Rosano, C.; Viale, M. Eur. J.
Med. Chem. 2011, 46, 5293−5309. (b) Ciayadi, R.; Potdar, M.;
Walton, K. L.; Harrison, C. A.; Kelso, G. F.; Harris, S. J.; Hearn, M. T.
W. Bioorg. Med. Chem. Lett. 2011, 21, 5642−5645. (c) Balbi, A.;
Anzaldi, M.; Maccio, C.; Aiello, C.; Mazzei, M.; Gangemi, R.;
Castagnola, P.; Miele, M.; Rosano, C.; Viale, M. Eur. J. Med. Chem.
2011, 46, 5293−5309.
(4) Hang, X.-C.; Fleetham, T.; Turner, E.; Brooks, J.; Li, J. Angew.
Chem., Int. Ed. 2013, 52, 6753−6756.
(5) For reviews of pyridine synthesis: (a) Bull, J. A.; Mousseau, J. J.;
Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642−2713.
(b) Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085−1094.
(6) For recent examples of transition-metal-catalyzed pyridine
synthesis: (a) Prechter, A.; Henrion, G.; Faudot dit Bel, P.; Gagosz,
F. Angew. Chem., Int. Ed. 2014, 53, 4959−4963. (b) Wu, Q.; Zhang, Y.;
Cui, S. Org. Lett. 2014, 16, 1350−1353. (c) Neely, J. M.; Rovis, T. J.
Am. Chem. Soc. 2014, 136, 2735−2738. (d) Lee, H.; Sim, Y.-K.; Park,
J.-W.; Jun, C.-H. Chem. - Eur. J. 2014, 20, 323−333. (e) Jiang, Y.; Park,
C.-M. Chem. Sci. 2014, 5, 2347−2351. (f) Wei, Y.; Yoshikai, N. J. Am.
Chem. Soc. 2013, 135, 3756−3759. (g) Neely, J. M.; Rovis, T. J. Am.
Chem. Soc. 2013, 135, 66−69. (h) Michlik, S.; Kempe, R. Angew.
Chem., Int. Ed. 2013, 52, 6326−6329. (i) Loy, N. S. Y.; Singh, A.; Xu,
X.; Park, C.-M. Angew. Chem., Int. Ed. 2013, 52, 2212−2216. (j) Zhao,
M.-N.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Chem. Commun. 2012,
48, 8105−8107. (k) Yamamoto, S.-i.; Okamoto, K.; Murakoso, M.;
Kuninobu, Y.; Takai, K. Org. Lett. 2012, 14, 3182−3185. (l) Gati, W.;
Rammah, M. M.; Rammah, M. B.; Couty, F.; Evano, G. J. Am. Chem.
Soc. 2012, 134, 9078−9081. (m) Wang, C.; Li, X.; Wu, F.; Wan, B.
Angew. Chem., Int. Ed. 2011, 50, 7162−7166. (n) Ohashi, M.; Takeda,
I.; Ikawa, M.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 18018−18021.
(o) Wang, Y.-F.; Chiba, S. J. Am. Chem. Soc. 2009, 131, 12570−12572.
(p) Chiba, S.; Xu, Y.-J.; Wang, Y.-F. J. Am. Chem. Soc. 2009, 131,
12886−12887. (q) Manning, J. R.; Davies, H. M. L. J. Am. Chem. Soc.
2008, 130, 8602−8603. (r) Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc.
2008, 130, 6918−6919. (s) Colby, D. A.; Bergman, R. G.; Ellman, J. A.
J. Am. Chem. Soc. 2008, 130, 3645−3651. (t) Barluenga, J.; Fernandez-
Rodriguez, M. A.; Garcia-Garcia, P.; Aguilar, E. J. Am. Chem. Soc. 2008,
130, 2764−2765.
(13) (a) Kurita, J.; Iwata, K.; Tsuchiya, T. Chem. Pharm. Bull. 1987,
35, 3166−3174. (b) Kurita, J.; Iwata, K.; Tsuchiya, T. J. Chem. Soc.,
Chem. Commun. 1986, 1188−1189.
(14) CCDC 1029899 (5aa), 1029900 (5bf), and 1029895 (2b) can
be obtained from The Cambridge Crystallographic Data Centre via
(15) Lu, T.; Lu, Z.; Ma, Z.-X.; Zhang, Y.; Hsung, R. P. Chem. Rev.
2013, 113, 4862−4904.
(16) We cannot deny the following pathway: a conjugate addition of
the nucleophile 3 to intermediate A directly delivers compound 4.
(7) For recent examples of organocatalyzed pyridine synthesis:
(a) Yoshida, M.; Mizuguchi, T.; Namba, K. Angew. Chem., Int. Ed.
2014, 53, 14550−14554. (b) Stark, D. G.; Morrill, L. C.; Yeh, P.-P.;
Slawin, A. M. Z.; O'Riordan, T. T. J. C.; Smith, A. D. Angew. Chem., Int.
Ed. 2013, 52, 11642−11646. (c) Shi, Z.; Loh, T.-P. Angew. Chem., Int.
Ed. 2013, 52, 8584−8587.
(8) For recent examples on metal-free pyridine synthesis: (a) Jiang,
Y.; Park, C.-M.; Loh, T.-P. Org. Lett. 2014, 16, 3432−3435.
(b) Desrosiers, J.-N.; Kelly, C. B.; Fandrick, D. R.; Nummy, L.;
Campbell, S. J.; Wei, X.; Sarvestani, M.; Lee, H.; Sienkiewicz, A.;
Sanyal, S.; Zeng, X.; Grinberg, N.; Ma, S.; Song, J. J.; Senanayake, C.
H. Org. Lett. 2014, 16, 1724−1727. (c) Xin, X.; Wang, D.; Li, X.; Wan,
B. Tetrahedron 2013, 69, 10245−10248. (d) Lei, C.-H.; Wang, D.-X.;
Zhao, L.; Zhu, J.; Wang, M.-X. J. Am. Chem. Soc. 2013, 135, 4708−
4711. (e) Huang, P.; Zhang, R.; Liang, Y.; Dong, D. Org. Lett. 2012,
14, 5196−5199. (f) Allais, C.; Lieby-Muller, F.; Constantieux, T.;
Rodriguez, J. Adv. Synth. Catal. 2012, 354, 2537−2544. (g) Kral, K.;
Hapke, M. Angew. Chem., Int. Ed. 2011, 50, 2434−2435. (h) Donohoe,
T. J.; Basutto, J. A.; Bower, J. F.; Rathi, A. Org. Lett. 2011, 13, 1036−
1039. (i) Sakai, T.; Danheiser, R. L. J. Am. Chem. Soc. 2010, 132,
13203−13205. (j) Sha, F.; Huang, X. Angew. Chem., Int. Ed. 2009, 48,
3458−3461.
(9) (a) Teo, Y.-C.; Yong, F.-F.; Sim, S. Tetrahedron 2013, 69, 7279−
7284. (b) Raba, A.; Anneser, M. R.; Jantke, D.; Cokoja, M.; Herrmann,
W. A.; Kuehn, F. E. Tetrahedron Lett. 2013, 54, 3384−3387. (c) Liu,
D
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