双功能配体促进的钯催化不对称醚化和胺化反应

doi:10.6023/A13040394

摘要/Abstract

研究双亚砜膦配体(BiSO-P)亚砜基团的Bronsted碱性在协同催化反应中的作用. ¹H NMR研究表明双亚砜膦与醇和胺等质子试剂形成氢键; 并将此类配体应用于钯催化的不对称醚化和胺化反应, 最高获得99% ee. 研究发现氢键的存在能有效提高反应的ee值, 配体亚砜基团在反应过程中同时起着Lewis和Bronsted碱的作用.

关键词: 手性双亚砜膦配体, 双功能, 氢键, 钯催化, 烯丙基醚化和胺化

A serious of bissulfoxide-phosphine ligands are examined on the Bronsted basicity of sulfinyl moiety. The effect of secondary binding property of the ligand is demostrated in Pd-catalyzed asymmetric allylic etherification and amination (up to 99% ee). And the application scope of this methodology to hydrogen-donor nucleophiles is investigated.

Key words: chiral bissulfoxide-phosphine ligands, bifunctional, hydrogen bond, Pd-catalysis, allylic etherification and amination

引用此文

杜乐, 曹鹏, 廖建. 双功能配体促进的钯催化不对称醚化和胺化反应[J]. 化学学报, 2013, 71(9): 1239-1242.

Du Le, Cao Peng, Liao Jian. Bifunctional Ligand Promoted Pd-Catalyzed Asymmetric Allylic Etherification/Amination[J]. Acta Chimica Sinica, 2013, 71(9): 1239-1242.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Sträter, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem., Int. Ed. 1996, 35, 2024; (b) Thomas, J. L.; Strickler, R. C.; Myers, R. P.; Covey, D. F. Biochemistry 1992, 31, 5522; (c) Wang, D. Biochemistry 1979, 18, 4449; (d) Reddy, K. R. C.; Turcu, F.; Schulte, A.; Kayastha, A. M.; Schuhmann, W. Anal. Chem. 2005, 77, 5063; (e) Paul, D.; Chatterjee, A.; Begley, T. P.; Ealick, S. E.; Biochemistry 2010, 49, 9922; (f) Haupt, C.; Weininger, U.; Kovermann, M.; Balbach, J. Biochemistry 2011, 50, 7321; (g) Kim, C.; Estrada, A. V.; Hesek, D.; Mobashery, S. Biochemistry 2007, 46, 5270.
[2] Reviews: (a) Ma, J. A.; Cahard, D. Angew. Chem., Int. Ed. 2004, 116, 4666; (b) Paull, D. H.; Abraham, C. J.; Scerba, M. T.; Alden-Danforth, E.; Lectka, T. Acc. Chem. Res. 2008, 41, 655; (c) Shibasaki, M.; Kanai, M.; Matsunaga, S.; Kumagai, N. Acc. Chem. Res. 2009, 42, 1117.
[3] (a) Rosenzweig, A. C.; Frederick, C. A.; Lippard, S. J.; Nordlund, P. Nature (London), 1993, 366, 537; (b) Stenkamp, R. E. Chem. Rev. 1994, 94, 715; (c) Jabri, E.; Carr, M. B.; Hausinger, R. P.; Karplus, P. A. Science (Washington, D. C.) 1995, 268, 998; (d) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853; (e) Goshe, A. J.; Crowley, J. D.; Bosnich, B. Helv. Chim. Acta 2001, 84, 2971; (f) Guilard, R.; Lopez, M. A.; Tabard, A.; Richard, P.; Lecomte, C.; Brandes, S.; Hutchison, J. E.; Collman, J. P. J. Am. Chem. Soc. 1992, 114, 9877; (g) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187; (h) Yamagiwa, N.; Hongbo, Q.; Shigeki, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13419; (i) Radlauer, M. R.; Buckley, A. K.; Henling, L. M.; Agapie, T. J. Am. Chem. Soc. 2013, 135, 3784; (j) Grudzień, K.; Malinska, M.; Barbasiewicz, M. Organometallics 2012, 31, 3636; (k) Too, P. C.; Chua, S. H.; Wong, S. H.; Chiba, S. J. Org. Chem. 2011, 76, 6159; (l) Kaizuka, K.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2010, 132, 15096.
[4] For reviews on bifunctional organocatalysts, see: (a) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520; (b) Connon, S. J. Chem. Commun. 2008, 2499; (c) Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638; (d) Palomo, C.; Oiarbide, M.; Lopez, R. Chem. Soc. Rev. 2009, 38, 632.
[5] For selected examples of bifunctional metal-tethered terminal functional group catalysts, see: (a) Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138; (b) Hayashi, T.; Kanehira, K.; Tsuchiya, H.; Kumada, M. J. Chem. Soc. Chem. Commun. 1982, 1162; (c) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113; (d) Ito, Y.; Sawamura, M.; Matsuoka, M.; Matsumoto, Y.; Hayashi, T. Tetrahedron Lett. 1987, 28, 4849; (e) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767; (f) Hayashi, T.; Konishi, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 107; (g) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723; (h) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206; (i) Lin, Y.-M.; Boucau, J.; Li, Z.; Casarotto, V.; Lin, J.; Nguyen, A. N.; Ehrmantraut, J. Org. Lett. 2007, 9, 567; (j) Yang, F.; Zhao, D.; Lan, J.; Xi, P.; Yang, L.; Xiang, S.; You, J. Angew. Chem., Int. Ed. 2008, 47, 5646; (k) Kull, T.; Cabrera, J.; Peters, R. Chem. Eur. J. 2010, 16, 9132; (l) Lang, K.; Park, J.; Hong, S. Angew. Chem., Int. Ed. 2012, 51, 1620.
[6] (a) Hayashi, T.; Tajika, M.; Tamao, K.; Kumada, M. J. Am. Chem. Soc. 1976, 98, 3718; (b) Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180; (c) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158; (d) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (e) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301; (f) Liu, H. Q.; Shi, L.; Chen, Q. A.; Wang, L.; Zhou, Y. G. Acta Chim. Sinica 2013, 71, 40. (刘洪强, 时磊, 陈庆安, 王磊, 周永贵, 化学学报, 2013, 71, 40.)
[7] Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. 1997, 36, 1236.
[8] DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668.
[9] Yang, T.; Ferrali, A.; Sladojevich, F.; Campbell, L.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 9140.
[10] Du, L.; Cao, P.; Xing, J. W.; Lou, Y. Z.; Jiang, L. Y.; Li, L. C.; Liao, J. Angew. Chem., Int. Ed. 2013, 52, 4207.
[11] Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986.
[12] Liao, J.; Sun, X.; Cui, X.; Yu, K.; Zhu, J.; Deng, J. G. Chem. Eur. J. 2003, 9, 2611.
[13] Pd-catalyzed asymmetric allylic substituted reactions using chiral sulfoxide-phosphine ligands finished in our group, see: (a) Chen, J. M.; Lang, F.; Li, D.; Cun, L. F.; Zhu, J.; Deng, J. G.; Liao, J. Tetrahedron: Asymmetry 2009, 20, 1953; (b) Xing, J. W.; Cao, P.; Liao, J. Tetrahedron: Asymmetry 2012, 23, 527.
[14] (a) Sun, X. H.; Peng, J.; Zhang, S. Y.; Zhou, Q. Q.; Dong, L.; Chen, Y. C. Acta Chim. Sinica 2012, 70, 1682; (b) Zhang, Z. F.; Xie, F.; Yang, B.; Yu, H.; Zhang, W. B. Chin. J. Org. Chem. 2011, 31, 429; (c) Wang, X. M.; Meng, F. Y.; Wang, Y.; Han, Z. B.; Chen, Y. J.; Liu, L.; Wang, Z.; Ding, K. L. Angew. Chem., Int. Ed. 2012, 51, 9276.
[15] Sawamura, M.; Nagata, H.; Sakamoto, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 2586.
[16] Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
[17] You, S. L.; Zhu, X. Z.; Luo, Y. M.; Hou, X. L.; Dai, L. X. J. Am. Chem. Soc. 2001, 123, 7471.
[18] (a) Lam, F. L.; Au-Yeung, T. T. L.; Kwong, F. Y.; Zhou, Z.; Wong, K. Y.; Chan, A. S. C. Angew. Chem., Int. Ed. 2008, 47, 1280; (b) Haight, A. R.; Stoner, E. J.; Peterson M. J.; Grover, V. K. J. Org. Chem. 2003, 68, 8092; (c) Kato, M.; Nakamura, T.; Ogata, K.; Fukuzawa, S. Eur. J. Org. Chem. 2009, 5232; (d) Liu, Z.; Du, H. F. Org. Lett. 2010, 12, 3054; (e) Roggen, M.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 5568; (f) Caldentey, X.; Pericàs, M. A. J. Org. Chem. 2010, 75, 2628; (g) Dai, L.; Li, X.; Yuan, H.; Li, X.; Li, Z.; Xu, D.; Fei, F.; Liu, Y.; Zhang, J.; Zhou, Z. Tetrahedron: Asymmetry 2011, 22, 1379; (h) Gavrilov, K. N.; Zheglov, S. V.; Shiryaev, A. A.; Groshkin, N. N.; Rastorguev, E. A.; Benetskiy, E. B.; Davankov, V. A. Tetrahedron Lett. 2011, 52, 964.