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化学学报  2015 

铜催化α-重氮酮对硼氢键的不对称插入反应

DOI: 10.6023/A15020125, PP. 326-329

Keywords: 不对称催化,卡宾插入反应,α-重氮酮,硼烷加合物,手性螺环配体

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Abstract:

手性有机硼化合物在有机合成、医药、材料等诸多领域中有广泛的应用,发展该类化合物的高效合成方法一直广受关注.此前,我们发展了过渡金属催化卡宾对硼氢键(B—H)的插入反应,并实现了α-重氮酯对B—H键的不对称插入反应.本文以手性螺环双噁唑啉配体和铜的络合物作为催化剂,首次实现了α-重氮酮对膦-硼烷加合物的B—H键不对称插入反应,获得了较高的收率和高达83%ee的对映选择性.该研究成果是为数不多的以α-重氮酮作为卡宾前体的不对称杂原子氢键插入反应,为手性α-硼取代酮化合物这类新的有机硼化合物的合成提供了有效方法.

References

[1]  (b) Moody, C. J. Angew. Chem., Int. Ed. 2007, 46, 9148.
[2]  (c) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
[3]  (d) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365.
[4]  (e) Zhu, S.-F.; Zhou, Q.-L. Nat. Sci. Rev. 2014, 1, 580. For recent examples, see:
[5]  (f) Song, X.-G.; Zhu, S.-F.; Xie, X.-L.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2013, 52, 2555.
[6]  (g) Xie, X.-L.; Zhu, S.-F.; Guo, J.-X.; Cai, Y.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2014, 53, 2978.
[7]  (h) Xu, B.; Zhu, S.-F.; Zhang, Z.-C.; Yu, Z.-X.; Ma, Y.; Zhou, Q.-L. Chem. Sci. 2014, 5, 1442.
[8]  (i) Zhu, Y.; Liu, X.; Dong, S.; Zhou, Y.; Li, W.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2014, 53, 1636.
[9]  Cheng, Q.-Q.; Zhu, S.-F.; Zhang, Y.-Z.; Xie, X.-L.; Zhou, Q.-L. J. Am. Chem. Soc. 2013, 135, 14094.
[10]  Li, X.; Curran, D. P. J. Am. Chem. Soc. 2013, 135, 12076.
[11]  For preparation and applications of α-diazoketones in catalytic asymmetric reactions, see: (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998.
[12]  (b) Doyle, M. P.; Eismont, M. Y.; Zhou, Q.-L. Russ. Chem. Bull. 1997, 46, 955.
[13]  (c) Kitagaki, S.; Anada, M.; Kataoka, O.; Matsuno, K.; Umeda, C.; Watanabe, N.; Hashimoto, S. J. Am. Chem. Soc. 1999, 121, 1417.
[14]  (d) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317.
[15]  (e) Hwang, C. H.; Chong, Y. H.; Song, S. Y.; Kwak, H. S.; Lee, E. Chem. Commun. 2004, 816.
[16]  (f) Suga, H.; Ishimoto, D.; Higuchi, S.; Ohtsuka, M.; Arikawa, T.; Tsuchida, T.; Kakehi, A.; Baba, T. Org. Lett. 2007, 9, 4359.
[17]  (g) Taber, D. F.; Tian, W. J. Org. Chem. 2008, 73, 7560.
[18]  (h) Denton, J. R.; Davies, H. M. L. Org. Lett. 2009, 11, 787.
[19]  (i) Xu, X.; Qian, Y.; Yang, L.; Hu, W. Chem. Commun. 2011, 47, 797. (j) Qian, Y.; Jing, C.; Liu, S.; Hu, W. Chem. Commun. 2013, 49, 2700.
[20]  (k) Taber, D. F.; Paquette, C. M.; Gu, P.; Tian, W. J. Org. Chem. 2013, 78, 9772.
[21]  (a) Ge, M.; Corey, E. J. Tetrahedron Lett. 2006, 47, 2319.
[22]  (b) Xu, B.; Zhu, S.-F.; Zuo, X.-D.; Zhang, Z.-C.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2014, 53, 3913.
[23]  For the development of chiral spiro ligands and catalysts, see: (a) Xie, J.-H.; Zhou, Q.-L. Acc. Chem. Res. 2008, 41, 581.
[24]  (b) Zhu, S.-F.; Zhou, Q.-L. In Privileged Chiral Ligands and Catalysts, Ed.: Zhou, Q.-L., Wiley-VCH, Weinheim, 2011, Chapter 4, p. 137.
[25]  (c) Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427. (谢建华,周其林, 化学学报, 2012, 70, 1427.)
[26]  NaBArF=sodium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate.
[27]  For preparation and applications of amine- and phosphine-borane adducts, see: (a) Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197.
[28]  (b) Staubitz, A.; Robertson, A. P. M.; Sloan, M. E.; Manners, I. Chem. Rev. 2010, 110, 4023.
[29]  (c) Staubitz, A.; Robertson, A. P. M.; Manners, I. Chem. Rev. 2010, 110, 4079.
[30]  For details, see Table S1 in Supporting Information.
[31]  (a) Imamoto, T.; Yamanoi, Y. Chem. Lett. 1996, 705.
[32]  (b) Kumaraswamy, G.; Rao, G. V.; RamaKrishna, G. Synlett 2006, 7, 1122.
[33]  (a) He, Z.; Yudin, A. K. J. Am. Chem. Soc. 2011, 133, 13770.
[34]  (b) St. Denis, J. D.; Zajdlik, A.; Tan, J.; Trinchera, P.; Lee, C. F.; He, Z.; Adachi, S.; Yudin, A. K. J. Am. Chem. Soc. 2014, 136, 17669 and references therein.
[35]  (a) Matteson, D. S. Stereodirected Synthesis with Organoboranes, Springer-Verlag, Berlin, Heidelberg, 1995.
[36]  (b) Organoboranes for Syntheses, Eds.: Ramachandran, P. V.; Brown, H. C., ACS Symposium Series 783, American Chemical Society, Washington, DC, 2001.
[37]  (c) Adams, J.; Kauffman, M. Cancer Invest. 2004, 22, 304.
[38]  (d) Wade, C. R.; Broomsgrove, A. E. J.; Aldridge, S.; Gabba?, F. P. Chem. Rev. 2010, 110, 3958.
[39]  (e) J?kle, F. Chem. Rev. 2010, 110, 3985.
[40]  (f) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417.
[41]  For reviews, see: (a) Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Syntheses via Boranes, Wiley-Interscience, New York, 1975.
[42]  (b) Carroll, A.-M.; O'Sullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609.
[43]  (c) Burks, H. E.; Morken, J. P. Chem. Commun. 2007, 4717.
[44]  (d) Calow, A. D. J.; Whiting, A. Org. Biomol. Chem. 2012, 10, 5485.
[45]  (e) Cid, J.; Gulyás, H.; Carbó, J. J.; Fernández, E. Chem. Soc. Rev. 2012, 41, 3558. For recent examples, see:
[46]  (f) Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894.
[47]  (g) Wu, H.; Radomkit, S.; O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 8277.
[48]  (h) Toure, M.; Chuzel, O.; Parrain, J.-L. J. Am. Chem. Soc. 2012, 134, 17892.
[49]  (i) Coombs, J. R.; Haeffner, F.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 11222. (j) Mlynarski, S. N.; Schuster, C. H.; Morken, J. P. Nature 2014, 505, 386.
[50]  For reviews, see: (a) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.

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