Chiral Phase-transfer Catalysts Bearing Multiple Hydrogen-bonding Donors Derived from Amino Acids: Efficient Catalysts for Diastereo- and Enantioselective Nitro-Mannich Reaction

Yu Liu , Zhonglin Wei , Yuxin Liu , Jingdong Wang , Jungang Cao , Dapeng Liang , Haifeng Duan , Yingjie Lin

Chemical Research in Chinese Universities ›› 2018, Vol. 34 ›› Issue (3) : 333 -337.

PDF
Chemical Research in Chinese Universities ›› 2018, Vol. 34 ›› Issue (3) :333 -337. DOI: 10.1007/s40242-018-8005-5
Article
Chiral Phase-transfer Catalysts Bearing Multiple Hydrogen-bonding Donors Derived from Amino Acids: Efficient Catalysts for Diastereo- and Enantioselective Nitro-Mannich Reaction
Author information +
History +
PDF

Keywords

Multiple hydrogen-bonding / Phase-transfer catalyst / Nitro-Mannich reaction / Aldehyde-derived N-Boc ketimine

Cite this article

Download citation ▾
Yu Liu, Zhonglin Wei, Yuxin Liu, Jingdong Wang, Jungang Cao, Dapeng Liang, Haifeng Duan, Yingjie Lin. Chiral Phase-transfer Catalysts Bearing Multiple Hydrogen-bonding Donors Derived from Amino Acids: Efficient Catalysts for Diastereo- and Enantioselective Nitro-Mannich Reaction. Chemical Research in Chinese Universities, 2018, 34(3): 333-337 DOI:10.1007/s40242-018-8005-5

登录浏览全文

4963

注册一个新账户 忘记密码

References

[1]

Takada K., Nagasawa K. Adv. Synth. Catal., 2009, 351(3): 345.

[2]

Sohtome Y., Takemura N., Takada K., Takagi R., Iguchi T., Naga-sawa K. Chem-Asian J., 2007, 2(9): 1150.

[3]

Sohtome Y., Hashimoto Y., Nagasawa K. Eur. J. Org. Chem., 2006, 2006(13): 2894.

[4]

Friestad G. K., Mathies A. K. Tetrahedron, 2007, 63(12): 2541.

[5]

Ballini R., Petrini M. Tetrahedron, 2004, 60(5): 1017.

[6]

Adam W., Makosza M., Saha-Möller C. R., Zhao C. G. Synlett., 1998, 1998(12): 1335.

[7]

Anderson J. C., Blake A. J., Howell G. P., Wilson C. J. Org. Chem., 2005, 70(2): 549.

[8]

Bennani Y. L., Hanessian S. Chem. Rev., 1997, 97(8): 3161.

[9]

Kizirian J. C. Chem. Rev., 2008, 108(1): 140.

[10]

Michalson E. T., Szmuszkovicz J. Progress in Drug Research, Springer, Berlin, 1989, 135.

[11]

Gravert D. J., Griffin J. H. J. Org. Chem., 1993, 58(4): 820.

[12]

Bernardi L., Bonini B. F., Dessole G., Fochi M., Comes-Franchini M., Gavioli S., Ricci A., Varchi G. J. Org. Chem., 2003, 68(4): 1418.

[13]

Tomioka K. Synthesis, 1990, 1990(7): 541.

[14]

Albano V. G., Bandini M., Monari M., Marcucci E., Piccinelli F., Umani-Ronchi A. J. Org. Chem., 2006, 71(17): 6451.

[15]

Das A., Kureshy R. I., Maity N. C., Subramanian P. S., Khan N. H., Abdi S. H. R., Suresh E., Bajaj H. C. Dalton Trans., 2014, 43(32): 12357.

[16]

Uraguchi D., Oyaizu K., Noguchi H., Ooi T. Chem-Asian^J., 2015, 10(2): 334.

[17]

Vara B. A., Mayasundari A., Tellis J. C., Danneman M. W., Arredondo V., Davis T. A., Min J., Finch K., Guy R. K., Johnston J. N. J. Org. Chem., 2014, 79(15): 6913.

[18]

Xu X., Furukawa T., Okino T., Miyabe H., Takemoto Y. Chem-Asian J., 2006, 12(2): 466.

[19]

Wang H. Y., Wang K. Y., Ren Y. F., Li N., Tang B., Zhao G. Adv. Synth. Catal., 2017, 359(11): 1819.

[20]

Liu Y. X., Liu Y., Wang J. D., Wei Z. L., Cao J. G., Liang D. P., Lin Y. J., Duan H. F. Tetrahedron Lett., 2017, 58(24): 2400.

[21]

Palomo C., Oiarbide M., Halder R., Laso A., López R. Angew. Chem. Int. Ed., 2006, 45(1): 117.

[22]

Tan C., Liu X. H., Wang L. W., Wang J., Feng X. M. Org. Lett., 2008, 10(22): 5305.

[23]

Nugent B. M., Yoder R. A., Johnston J. N. J. Am. Chem. Soc., 2004, 126(11): 3418.

[24]

Palomo C., Oiarbide M., Laso A., López R. J. Am. Chem. Soc., 2005, 127(50): 17622.

[25]

Uraguchi D., Sakaki S., Ooi T. J. Am. Chem. Soc., 2007, 129(41): 12392.

[26]

Handa S., Gnanadesikan V., Matsunaga S., Shibasaki M. J. Am. Chem. Soc., 2010, 132(13): 4925.

[27]

Gomez-Bengoa E., Linden A., López R., Múgica-Mendiola I., Oiarbide M., Palomo C. J. Am. Chem. Soc., 2008, 130(25): 7955.

[28]

Davis T. A., Wilt J. C., Johnston J. N. J. Am. Chem. Soc., 2010, 132(9): 2880.

[29]

Rampalakos C., Wulff W. D. Adv. Synth. Catal., 2008, 350(11/12): 1785.

[30]

Yamada K. i, Harwood S. J., Gröger H., Shibasaki M. Angew. Chem. Int. Ed., 1999, 38(23): 3504.

[31]

Wang B., Xu T., Zhu L., Lan Y., Wang J. D., Lu N., Wei Z. L., Lin Y. J., Duan H. F. Org. Chem. Front., 2017, 7(4): 1266.

[32]

Wei Y., He W., Liu Y. L., Liu P., Zhang S. Y. Org. Lett., 2012, 14(3): 704.

[33]

Johnson K. M., Rattley M. S., Sladojevich F., Barber D. M., Nuñez M. G., Goldys A. M., Dixon D. J. Org. Lett., 2012, 14(10): 2492.

[34]

Fini F., Sgarzani V., Pettersen D., Herrera R. P., Bernardi L. RicciA., Angew. Chem., 2005, 117(48): 8189.

[35]

Cao D. D., Chai Z., Zhang J. X., Ye Z. Q., Xiao H., Wang H. Y., Chen J. H., Wu X. Y., Zhao G. Chem. Commun., 2013, 49(53): 5972.

[36]

Jiang X. X., Zhang Y. F., Wu L., Zhang G., Liu X., Zhang H. L., Fu D., Wang R. Adv. Synth. Catal., 2009, 351(13): 2096.

[37]

Wang H. Y., Chai Z., Zhao G. Tetrahedron, 2013, 69(25): 5104.

[38]

Wang H. Y., Zhang J. X., Cao D. D., Zhao G. ACS Catalysis, 2013, 3(10): 2218.

[39]

Wang C. J., Dong X. Q., Zhang Z. H. J. Am. Chem. Soc., 2008, 130(27): 8606.

[40]

Davis T. A., Johnston J. N. Chem. Sci., 2011, 2(6): 1076.

[41]

Lu N., Li R. X., Wei Z. L., Cao J. G., Liang D. P., Lin Y. J., Duan H. F. J. Org. Chem., 2017, 82(9): 4668.

[42]

Liu Y. L., Wang X., Wang X. Y., He W. Org. Biomol. Chem., 2014, 12(20): 3163.

[43]

Ma C. H., Kang T. R., He L., Liu Q. Z. Eur. J. Org. Chem., 2014, 2014(19): 3981.

[44]

Wu X. Y., Liu Q., Liu Y., Wang Q., Zhang Y., Chen J., Cao W. G., Zhao G. Adv. Synth. Catal., 2013, 355(13): 2701.

[45]

Dong Z., Yan C., Gao Y. Z., Dong C. E., Qiu G. F., Zhou H. B. Adv. Synth. Catal., 2015, 357(9): 2132.

[46]

Zhong F. R., Han X. Y., Wang Y. Q., Lu Y. X. Angew. Chem., 2011, 123(34): 7983.

[47]

Qiu S., Tan C. H., Jiang Z. Y. Beilstein J. Org. Chem., 2016, 12(1): 2293.

[48]

Cowen B. J., Miller S. J. J. Am. Chem. Soc., 2007, 129(36): 10988.

[49]

Han X. Y., Wang Y. Q., Zhong F. R., Lu Y. J. Am. Chem. Soc., 2011, 133(6): 1726.

[50]

Han X. Y., Zhong F. R., Wang Y. Q., Lu Y. X. Angew. Chem. Int. Ed., 2012, 51(3): 767.

[51]

Huang W. B., Tian H., Xu H., Zheng L. Y., Liu Q. W., Zhang S. Q. Catal. Lett., 2011, 141(6): 872.

[52]

Liu Y. X., Wei Z. L., Liu Y., Cao J. G., Liang D. P., Lin Y. J., Duan H. F. Org. Biomol. Chem., 2017, 15(43): 9234.

[53]

Wang B., Liu Y. X., Sun C., Wei Z. L., Cao J. G., Liang D. P., Lin Y. J., Duan H. F. Org. Lett., 2014, 16(24): 6432.

[54]

Dong X. Q., Teng H. L., Wang C. J. Org. Lett., 2009, 11(6): 1265.

[55]

Wang C. J., Zhang Z. H., Dong X. Q., Wu X. J. Chem. Commun., 2008, 130(12): 1431.

[56]

Shi X., He W., Li H., Zhang X., Zhang S. Y. Tetrahedron Lett., 2011, 52(25): 3204.

PDF

215

Accesses

0

Citation

Detail

Sections
Recommended

/