[1] Gregory, R. J. H. Chem. Rev. 1999, 99, 3649.
[2] Jones, S. B.; Simmons, B.; Mastracchio, A.; MacMillan, D. W. C. Nature 2011, 475, 183.
[3] (a) Kurono, N.; Ohkuma, T. ACS Catal. 2016, 6, 989;
(b) Fu, Y.; Hou, B.; Zhao, X.; Du, Z.; Hu, Y. Chin. J. Org. Chem. 2015, 35, 2507. (傅颖, 侯博, 赵兴玲, 杜正银, 胡雨来, 有机化学, 2015, 35, 2507);
(c) Wang, W.; Liu, X.; Lin, L.; Feng, X. Eur. J. Org. Chem. 2010, 4751;
(d) North, M.; Usanov, D. L.; Young, C. Chem. Rev. 2008, 108, 5146;
(e) Brunel, J.-M.; Holmes, I. P. Angew. Chem., Int. Ed. 2004, 43, 2752.
[4] (a) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 541;
(b) Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Chem. Soc. Chem. Commun. 1991, 1752;
(c) Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515;
(d) Bolm, C.; Muller, P. Tetrahedron Lett. 1995, 36, 1625;
(e) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264;
(f) Belokon, Y. N.; Flego, M.; Ikonnikov, N. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M. J. Chem. Soc. 1997, 1293;
(g) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron:Asymmetry 1997, 8, 1279;
(h) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641;
(i) Belokon, Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva, G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968;
(j) Belokon, Y. N.; North, M.; Parsons, T. Org. Lett. 2000, 2, 1617;
(k) You, J.-S.; Gau, H.-M.; Choi, M. K. Chem. Commun. 2000, 1963;
(l) Holmes, I. P.; Kagan, H. B. Tetrahedron Lett. 2000, 41, 7457;
(m) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106;
(n) Qin, Y. C.; Liu, L.; Pu, L. Org. Lett. 2005, 7, 2381;
(o) Hatano, M.; Ikeno, T.; Miyamoto, T.; Ishihara, K. J. Am. Chem. Soc. 2005, 127, 10776;
(p) Moreno, R. M.; Rosol, M.; Moyano, A. Tetrahedron:Asymmtry 2006, 17, 1089;
(q) Kurono, N.; Arai, K.; Uemura, M.; Ohkuma, T. Angew. Chem., Int. Ed. 2008, 47, 6643;
(r) Yoshinaga, K.; Nagata, T. Adv. Synth. Catal. 2009, 351, 1495;
(s) Dang, D.; Wu, P.; He, C.; Xie, Z.; Duan, C. J. Am. Chem. Soc. 2010, 132, 14321;
(t) Chu, C.-Y.; Hsu, C.-T.; Lo, P. H.; Uang, B.-J. Tetrahedron:Asymmetry 2011, 22, 1981;
(u) Blocka, E.; Bosiak, M. J.; Welniak, M.; Ludwiczak, A.; Wojtczak, A. Tetrahedron:Asymmetry 2014, 25, 554;
(v) Mo, K.; Yang, Y.; Cui, Y. J. Am. Chem. Soc. 2014, 136, 1746.
[5] (a) Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 10521;
(b) Kende, A. S.; Liu, K.; Kaldor, I.; Dorey, G.; Koch, K. J. Am. Chem. Soc. 1995, 117, 8258.
[6] (a) Yang, Z. H.; Wang, L. X.; Zhou, Z. H.; Zhou, Q. L.; Tang, C. C. Tetrahedron:Asymmetry 2001, 12, 1579;
(b) He, K.; Zhou, Z.; Wang, L.; Li, K.; Zhao, G.; Zhou, Q.; Tang, C. Tetrahedron 2004, 60, 10505;
(c) Zeng, Z.; Zhao, G.; Gao, P.; Tang, H.; Chen, B.; Zhou, Z.; Tang, C. Catal. Commun. 2007, 8, 1443;
(d) Lv, C.; Wang, S.; Wu, M.; Xia, C.; Sun, W. Tetrahedron:Asymmetry 2010, 21, 1869;
(e) Wen, Y. Q.; Ren, W. M.; Lu, X. B. Chin. Chem. Lett. 2011, 22, 1285.
(f) Zeng, Z.; Zhao, G.; Zhou, Z.; Tang, C. Eur. J. Org. Chem. 2008, 1615;
(g) Yang, H. Q.; Zhang, L.; Wang, P.; Yang, Q. H.; Li, C. Green Chem. 2009, 11, 257;
(h) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356;
(i) Wei, Y. L.; Huang, W. S.; Cui, Y. M.; Yang, K. F.; Xua, Z.; Xu, W. L. RSC Adv. 2015, 5, 3098.
[7] (a) Li, Y.; He, B.; Qin, B.; Feng, X.; Zhang, G. J. Org. Chem. 2004, 69, 7910;
(b) Chen, F. X.; Feng, X. M. Synlett 2005, 892;
(c) Wen, Y. H.; Huang, X.; Huang, J. L.; Xiong, Y.; Qin, B.; Feng, X. M. Synlett 2005, 2445;
(d) Liu, Y. L.; Liu, X. H.; Xin, J. G.; Feng, X. M. Synlett 2006, 1085;
(e) Wang, W.; Zhou, S.; Liu, X.; Feng, X. Tetrahedron 2007, 63, 5129;
(f) Liu, X. H.; Lin, L. L.; Feng, X. M. Acc. Chem. Res. 2011, 44, 574;
(g) Liu, X.; Lin, L.; Feng, X. Org. Chem. Front. 2014, 1, 298.
[8] (a) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10;
(b) Yuan, Y.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2003, 42, 5478;
(c) Du, H.; Ding, K. Org. Lett. 2003, 5, 1091;
(d) Ding, K.; Du, H.; Yuan, Y.; Long, J. Chem. Eur. J. 2004, 10, 2872.
[9] Zhang, Z.; Wang, Z.; Zhang, R.; Ding, K. Angew. Chem., Int. Ed. 2010, 49, 6746.
[10] (a) Luo, H. Chin. J. Org. Chem. 2011, 31, 1(罗海南, 有机化学, 2011, 31, 1);
(b) Soleimani, E. Synlett 2007, 18, 1625;
(c) Romero-Hernández, L. L. Synlett 2015, 26, 563;
(d) Gawronski, J.; Wascinska, N.; Gajewy, J. Chem. Rev. 2008, 108, 5227;
(e) Fuchs, P. L. Handbook of Reagents for Organic Syntehsis, Reagents for Silicon-Mediated Organic Synthesis, John Wiley & Sons, New Deli, Singapore, 2011.
[11] (a) Liu, Y.-L.; Shi, T.-D.; Zhou, F.; Zhao, X.-L.; Wang, X.; Zhou, J. Org. Lett. 2011, 13, 3826;
(b) Liu, Y.-L.; Zhou, J. Chem. Commun. 2013, 49, 4421;
(c) Liu, Y.-L.; Zhou, F.; Cao, J.-J.; Ji, C.-B.; Ding, M.; Zhou, J. Org. Biomol. Chem. 2010, 8, 3847. For a mini-review:
(d) Liu, Y.-L.; Zhou, J. Synthesis 2015, 1210.
[12] Zhao, Y.-L.; Cao, Z.-Y.; Zeng, X.-P.; Shi, J.-M.; Yu, Y.-H.; Zhou, J. Chem. Commun. 2016, 52, 3943.
[13] Cao, J.-J.; Zhou, F.; Zhou, J. Angew. Chem., Int. Ed. 2010, 49, 4976.
[14] Zeng, X.-P.; Cao, Z.-Y.; Wang, X.; Chen, L.; Zhou, F.; Zhu, F.; Wang, C.-H.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 416.
[15] Zeng, X.-P.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 8730.
[16] (a) Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691;
(b) Zhou, Q.-L. Privileged Chiral Ligands and Catalysts, Wiley-VCH Verlag & Co. KGaA, Weinheim, Germany, 2011.
[17] (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315;
(b) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442;
(c) Wang, S.-X.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Org. Lett. 2007, 9, 3615;
(d) Wang, S.-X.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Angew. Chem., Int. Ed. 2008, 47, 388;
(e) Yue, T.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Angew. Chem., Int. Ed. 2008, 47, 9454;
(f) Bandini, M.; Fagioli, M.; Garavelli, M.; Melloni, A.; Trigari, V.; Umani-Ronchi, A. J. Org. Chem. 2004, 69, 7511;
(g) Jakhar, A.; Sadhukhan, A.; Khan, N. H.; Saravanan, S.; Kureshy, R. I.; Abdi, S. H. R.; Bajaj, H. C. ChemCatChem 2014, 6, 2656. For selected reviews:
(h) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421;
(i) Larrow, J. F.; Jacobsen, E. N. Topics Organomet. Chem. 2004, 6, 123.
(j) Baleizão, C.; Garcia, H. Chem. Rev. 2006, 106, 3987.
[18] Kim, S. S. Pure Appl. Chem. 2006, 78, 977.
[19] We tried the one-pot sequential asymmetric cyanosilylation/chloromethyl transfer reaction, and the corresponding aromatic methyl ketones were obtained as the major product. For the proposed mechanism, see supporting information:???A16100541-1???
[20] According to the reviewer's suggestion, we investigated the effect of Ph3PO, which could generate from side Wittig reaction, on the cyanation of p-chlorobenzaldehyde and TMSCN. NMR analysis of the crude reaction mixture showed the signals of both Ph3PO and ylide, suggesting ylide 2a was not consumed at the end of the cyanation. The addition of 6 mol% of Ph3PO did not appreciably accelerate the cyanation reaction. When Ph3PO and (salen)AlCl were used as the catalysts, in the absence of ylide 2a, the reaction could also proceed well, albeit in a lower reaction rate (finish within 2 days and afford 91% ee). This suggested that the Ph3PO produced from side Wittig reaction had little acceleration effect on the reactivity, but slightly decreased the enantioselectivity of the reaction. (Cheng, B.)???A16100541-2??? |