[1] (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis;Tetrahedron Organic Chemistry Series 9, Pergamon Press, Oxford, U. K., 1992.
(b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
(c) Zhang, Z.; Xie, F.; Yang, B.; Yu, H.; Zhang, W. Chin. J. Org. Chem. 2011, 31, 429. (张振锋, 谢芳, 杨波, 余焓, 张万斌, 有机化学, 2011, 31, 429.)
(d) Ying, A.; Wu, C.; Fu, Y.; Ren, S.; Liang, H. Chin. J. Org. Chem. 2012, 32, 1587. (应安国, 武承林, 付永前, 任世斌, 梁华定, 有机化学, 2012, 32, 1587.)
[2] For reviews, see: (a) Tomioka, K.; Nagaoka, Y. Comprehensive Asymmetric Catalysis, Eds.: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Springer, New York, 1999, p. 1105
(b) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
(c) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 2, 171.
(d) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry, Ed.: Krause, N., VCH, Weinheim, Germany, 2002, p. 224.
(e) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 67, 3221.
(f) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
(g) Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 5560.
(h) López, F.; Minnaard, A. J.; Feringa, B. L. Acc. Chem. Res. 2007, 40, 179.
(i) López, F.; Minnaard, A. J.; Feringa, B. L. In The Chemistry of Organomagnesium Compounds, Eds.: Rappoport, Z.; Marek, I., Wiley, Chichester, U. K., 2008; Part 2, Chapter 17.
(j) Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824.
[3] For reviews, see: (a) Tian, P.; Dong, H.-Q.; Lin, G.-Q. ACS Catal. 2012, 2, 95.
(b) Partyka, D. V. Chem. Rev. 2011, 111, 1529.
(c) Berthon, G.; Hayashi, T. In Catalytic Asymmetric Conjugate Reactions, Ed.: Córdova, A., Wiley-VCH, Weinheim, Germany, 2010, Chapter 1, p. 1.
(d) Edwards, H. J.; Hargrave, J. D.; Penrose, S. D.; Frost, C. G. Chem. Soc. Rev. 2010, 39, 2093.
(e) Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840.
(f) Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313.
(g) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
(h) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
(i) Bolm, C.; Hildebrand, J. P.; Muñiz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284.
(j) Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279.
(k) Enders, D.; Lüttgen, K.; Narine, A. A. Synthesis 2007, 959.
(l) Hayashi, T. Synlett 2001, 879.
(m) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
(n) Shintani, R.; Tokunaga, N.; Doi, H.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 6240.
[4] Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
[5] Early studies of α,β-unsaturated ketones, see: (a) Reetz, M. T.; Moulin, D.; Gosberb, A. Org. Lett. 2001, 3, 4083.
(b) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932.
(c) Boiteau, J. G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 681.
(d) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 1040.
(e) Defieber, C.; Paquin, J.-F.; Serna, S.; Carreira, E. M. Org. Lett. 2004, 6, 3873.
[6] α,β-Unsaturated Esters, Amides, and Aldehydes: (a) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
(b) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
(c) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852.
(d) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944.
(e) Paquin, J.-F.; Defieber, C.; Stephenson, C. R. J.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 10850.
[7] Alkenylphosphonates: Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591.
[8] Nitroalkenes: Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
[9] Alkenylheteroarenes and alkenylarenes: (a) Pattison, G.; Piraux, G.; Lam, H. W. J. Am. Chem. Soc. 2010, 132, 14373.
(b) Saxena, A.; Lam, H. W. Chem. Sci. 2011, 2, 2326.
[10] For reviews, see: (a) Simpkins, N. S. Tetrahedron 1990, 46, 6951.
(b) Rayner, C. M. Contemp. Org. Synth. 1996, 3, 499.
(c) Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
(d) Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
(e) Bäckvall, J.-E.; Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 1998, 98, 2291.
(f) Meadows, D. C.; Gervay-Hague, J. Med. Res. Rev. 2006, 26, 793.
(j) Tozer, M. J.; Harper, E. A.; Kalindjian, S. B.; Pether, M. J.; Shankley, N. P.; Watt, G. F. Bioorg. Med. Chem. Lett. 1999, 9, 1825.
(h) Tamamura, H.; Koh, Y.; Ueda, S.; Sasaki, Y.; Yamasaki, T.; Aoki, M.; Maeda, K.; Watai, Y.; Arikuni, H.; Otaka, A.; Mitsuya, H.; Fujii, N. J. Med. Chem. 2003, 46, 1764.
(i) Hanessian, S.; Sailes, H.; Therrien, E. Tetrahedron 2003, 59, 7047.
(j) Zajac, M.; Peters, R. Chem. Eur. J. 2009, 15, 8204.
[11] For recent examples, see: (a) Enders, D.; Müller, S. F.; Raabe, G. Angew. Chem., Int. Ed. 1999, 38, 195.
(b) Grimaud, L.; Rotulo, D.; Ros-Perez, R.; Guitry-Azam, L.; Prunet, J. Tetrahedron Lett. 2002, 43, 7477.
(c) Luis, L. A.; Krische, M. J. Synthesis 2004, 2579.
(d) Tsui, G. C.; Lautens, M. Angew. Chem., Int. Ed. 2010, 49, 8938.
(e) García Ruano, J. L.; Schöpping, C.; Alvarado, C.; Alemán, J. Chem. Eur. J. 2010, 16, 8968.
(f) So, C. M.; Kume, S.; Hayashi, T. J. Am. Chem. Soc. 2013, 135, 10990.
(g) Lu, J.; Ye, J.; Duan, W. Chem. Commun. 2014, 50, 698.
[12] For examples of copper-catalyzed asymmetric transformations, see: (a) Llamas, T.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2007, 46, 3329.
(b) Desrosiers, J.-N.; Charette, A. B. Angew. Chem., Int. Ed. 2007, 46, 5955.
(c) Bechara, W. S.; Charette, A. B. Org. Lett. 2008, 10, 2315.
(d) Bos, P. H.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2008, 10, 4219.
(e) Bos, P. H.; Maciá, B.; Fernández-Ibáñez, M.Á.; Minnaard, A. J.; Feringa, B. L. Org. Biomol. Chem. 2010, 8, 47.
[13] For a review of organocatalytic asymmetric addition to alkenyl sulfones, see: Nielsen, M.; Jacobsen, C. B.; Holub, N.; Paixão, M. W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2010, 49, 2668.
[14] (a) Mauleón, P.; Carretero, J. C. Org. Lett. 2004, 6, 3195.
(b) Mauleón, P.; Carretero, J. C. Chem. Commun. 2005, 41, 4961.
(c) Mauleón, P.; Alonso, I.; Rivero, M. R.; Carretero, J. C. J. Org. Chem. 2007, 72, 9924.
[15] Nishimura, T.; Takiguchi, Y.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 9086.
[16] (a) Jin, S.-S.; Wang, H.; Xu, M.-H. Chem. Commun. 2011, 47, 7230.
(b) Qi, W.-Y.; Zhu, T.-S.; Xu, M.-H. Org. Lett. 2011, 13, 3410.
(c) Jin, S.-S.; Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 1764.
(d) Zhu, T.-S.; Jin, S.-S.; Xu, M.-H. Angew. Chem., Int. Ed. 2012, 51, 780.
(e) Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 9158.
(f) Zhu, T.-S.; Chen, J.-P.; Xu, M.-H. Chem. Eur. J. 2013, 19, 865.
(g) Wang, H.; Jiang, T.; Xu, M.-H. J. Am. Chem. Soc. 2013, 135, 971.
(h) Wang, H.; Xu, M.-H. Synthesis 2013, 45, 2125.
(i) Li, Y.; Zhu, D.-X.; Xu, M.-H. Chem. Commun. 2013, 49, 11659.
(j) Li, Y.; Xu, M.-H. Chem. Commun. 2014, 50, 3771.
[17] Yu, Y.-N.; Xu, M.-H. Org. Chem. Front. 2014, DOI: 10. 1039/c4qo00135d.
[18] Selected early examples of the use of chiral phosphorus-based olefin ligands: (a) Maire, P.; Deblon, S.; Breher, F.; Geier, J.; Böhler, C.; Rügger, H.; Schönberg, H.; Grtrümacher, H. Chem. Eur. J. 2004, 10, 4198.
(b) Shintani, R.; Duan, W.-L.; Nagano, T.; Okada, A.; Grützmacher, T. Angew. Chem., Int. Ed. 2005, 44, 4611.
(c) Defieber, C.; Ariger, M. A.; Moriel, P.; Carreira, E. M. Angew. Chem. Int. Ed. 2007, 46, 3139.
(d) Mariz, R.; Briceño, A.; Dorta, R.; Dorta, R. Organometallics 2008, 27, 6605.
(e) Liu, Z.; Du, H. Org. Lett. 2010, 12, 3054. |