Beilstein J. Org. Chem. 2011, 7, 1100–1107.
25.Liu, X.-Y.; Li, C.-H.; Che, C.-M. Org. Lett. 2006, 8, 2707–2710.
Hong Kong SAR of China (Area of Excellence Scheme, AoE/P-
10/01). Y.-P. Xiao thanks the Croucher Foundation of Hong
Kong for a postgraduate studentship and the External Coopera-
tion Program of CAS (GJHZ200816). We thank the referees for
their insightful suggestions concerning this paper.
26.Van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54,
27.Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41,
28.Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33,
References
29.Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev.
1. Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395–403.
30.Shi, Y.; Peterson, S. M.; Haberaecker, W. W., III; Blum, S. A.
31.Shi, Y.; Ramgren, S. D.; Blum, S. A. Organometallics 2009, 28,
2. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180–3211.
3. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239–3265.
32.Hashmi, A. S. K.; Lothschütz, C.; Döpp, R.; Rudolph, M.;
Ramamurthi, T. D.; Rominger, F. Angew. Chem., Int. Ed. 2009, 48,
4. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108,
5. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108,
33.Shi, Y.; Roth, K. E.; Ramgren, S. D.; Blum, S. A. J. Am. Chem. Soc.
34.Egi, M.; Yamaguchi, Y.; Fujiwara, N.; Akai, S. Org. Lett. 2008, 10,
6. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232–5241.
7. Corma, A.; Leyva-Perez, A.; Sabater, M. J. Chem. Rev. 2011, 111,
35.Ye, L.; Zhang, L. Org. Lett. 2009, 11, 3646–3649.
8. Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994–2009.
36.Weber, D.; Tarselli, M. A.; Gagné, M. R. Angew. Chem., Int. Ed. 2009,
9. Bandini, M. Chem. Soc. Rev. 2011, 40, 1358–1367.
37.Weber, D.; Gagne, M. R. Org. Lett. 2009, 11, 4962–4965.
10.LaLonde, R. L.; Brenzovich, J. W. E.; Benitez, D.; Tkatchouk, E.;
Kelley, K.; Goddard, W. A., III; Toste, F. D. Chem. Sci. 2010, 1,
38.Ramon, R. S.; Bosson, J.; Diez-Gonzalez, S.; Marion, N.; Nolan, S. P.
39.Dai, L.-Z.; Shi, M. Chem.–Eur. J. 2010, 16, 2496–2502.
11.Yang, C.-G.; He, C. J. Am. Chem. Soc. 2005, 127, 6966–6967.
40.Aksın-Artok, Ö.; Krause, N. Adv. Synth. Catal. 2011, 353, 385–391.
12.Nguyen, R.-V.; Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 2397–2399.
41.Tietze, L. F.; Gordon, B.; Kersten, G. M., Eds. Domino Reactions in
Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
42.Jung, H. H.; Floreancig, P. E. J. Org. Chem. 2007, 72, 7359–7366.
13.Hashmi, A. S. K.; Schäfer, S.; Wölfle, M.; Diez Gil, C.; Fischer, P.;
Laguna, A.; Blanco, M. C.; Gimeno, M. C. Angew. Chem., Int. Ed.
14.Zhang, X.; Corma, A. Chem. Commun. 2007, 3080–3082.
43.Huang, J.; Huang, X.; Liu, B. Org. Biomol. Chem. 2010, 8, 2697–2699.
15.Aponick, A.; Li, C.-Y.; Biannic, B. Org. Lett. 2008, 10, 669–671.
44.Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4,
16.Widenhoefer, R. A.; Han, X. Eur. J. Org. Chem. 2006, 4555–4563.
45.Lin, G.-Y.; Li, C.-W.; Hung, S.-H.; Liu, R.-S. Org. Lett. 2008, 10,
17.Widenhoefer, R. A. Chem.–Eur. J. 2008, 14, 5382–5391.
46.The control experiment was suggested by one reviewer. We used the
product 3a with a diastereomeric ratio of 1.5:1 heated with 5 mol % of
(t-Bu)2(o-diphenyl)PAuCl and 10 mol % of AgOTf in toluene at 90 °C,
indeed, we could get a 5.2:1 mixture of two diastereomers after 20 h.
The effect of catalyst loading on diastereoselectivity may be due to the
silver salt acting as a lewis acid promoting the isomeration of
cis-configuration to trans-configuration.
18.Krause, N.; Belting, V.; Deutsch, C.; Erdsack, J.; Fan, H. T.; Gockel, B.;
Hoffmann-Röder, A.; Morita, N.; Volz, F. Pure Appl. Chem. 2008, 80,
19.Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884–6885.
20.Nguyen, R.-V.; Yao, X.-Q.; Bohle, D. S.; Li, C.-J. Org. Lett. 2005, 7,
47.Gaunt, M. J.; Spencer, J. B. Org. Lett. 2001, 3, 25–28.
21.Zhou, C.-Y.; Che, C.-M. J. Am. Chem. Soc. 2007, 129, 5828–5829.
22.Wang, M.-Z.; Wong, M.-K.; Che, C.-M. Chem.–Eur. J. 2008, 14,
23.Xiao, Y.-P.; Liu, X.-Y.; Che, C.-M. J. Organomet. Chem. 2009, 694,
24.Xiao, Y.-P.; Liu, X.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2011, 50,
1106