K3PO4-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds

doi:10.1007/s40242-019-9137-y

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (6): 1002-1007.doi: 10.1007/s40242-019-9137-y

• Articles • Previous Articles Next Articles

K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds

CHEN Zhanguo, WEN Ting, HOU Dan

Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, P. R. China

Received:2019-05-17 Revised:2019-07-09 Online:2019-12-01 Published:2019-11-29
Contact: CHEN Zhanguo E-mail:chzhg@snnu.edu.cn
Supported by:
Supported by the Natural Science Foundation of Shaanxi Province, China(No.2009JM2001) and the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University, China(No.2008CXB009).

Abstract

Abstract: An easy and efficient method for the synthesis of multisubstituted cyclopropane derivatives from electron-deficicent alkenes with 2-bromo-1,3-propanedione compounds was described. For this method, ethyl α-cyanocinnamate derivatives 1 and β,β-dicyanostyrene derivatives 4 can all smoothly react with 2-bromo-1,3-propanedione compounds 2 to afford the corresponding multisubstituted cyclopropane derivatives 3 and 5 in good to excellent yields(up to 100%) promoted by anhydrous K₃PO₄ in DMF at room temperature, respectively. A possible mechanism of this reaction was proposed. Structures of all the products were confirmed by ¹H NMR, ¹³C NMR and HRMS.

Key words: Cyclopropanation, Multisubstituted cyclopropane derivative, Electron-deficicent alkene, 2-Bromo-1,3-propanedione compound

CHEN Zhanguo, WEN Ting, HOU Dan. K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds[J]. Chemical Research in Chinese Universities, 2019, 35(6): 1002-1007.

References

[1] Lautens M., Klute W., Tam W., Chem. Rev., 1996, 96(1), 49
[2] Carson C. A., Kerr M. A., Chem. Soc. Rev., 2009, 38(11), 3051
[3] Chen D. Y. K., Pouwer R. H., Richard J. A., Chem. Soc. Rev., 2012, 41(13), 4631
[4] Kim H. Y., Walsh P. J., Acc. Chem. Res., 2012, 45(9), 1533
[5] Pan L., Liu X. H., Shi Y. X., Wang B. L., Wang S. H., Li B. J., Li Z. M., Chem. Res. Chinese Universities, 2010, 26(3), 389
[6] Faust R., Angew Chem. Int. Ed., 2001, 40(12), 2251
[7] Donaldson W. A., Tetrahedron, 2001, 57(41), 8589
[8] Little R. D., Dawson J. R., J. Am. Chem. Soc., 1978, 100(14), 4607
[9] Little R. D., Dawson J. R., Tetrahedron Lett., 1980, 21(27), 2609
[10] Caine D., Tetrahedron, 2001, 57(14), 2643
[11] Warner D. T., J. Org. Chem., 1959, 24, 1536
[12] McCoy L. L., J. Org. Chem., 1964, 29(1), 240
[13] Wong H. N. C., Hon M. Y., Tse C. W., Yip Y. C., Tanko J., Hudlicky T., Chem. Rev., 1989, 89(1), 165
[14] Reissig H. U., Zimmer R., Chem. Rev., 2003, 103(4), 1151
[15] Wurz R. P., Charette A. B., Org. Lett., 2005, 7(12), 2313
[16] Carson C. A., Kerr M. A., Chem. Soc. Rev., 2009, 38(11), 3051
[17] Simone F. D., Waser J., Synthesis, 2009, (20), 3353
[18] Lebel H., Marcoux J. F., Molinaro C., Charette A. B., Chem. Rev., 2003, 103(4), 977
[19] Rubin M., Rubina M., Gevorgyan V., Chem. Rev., 2007, 107(7), 3117
[20] Rubin M., Rubina M., Gevorgyan V., Synthesis, 2006, (8), 1221
[21] Long J., Yuan Y., Shi Y., J. Am. Chem. Soc., 2003, 125(45), 13632
[22] Aggarwal V. K., Fang G. Y., Meek G., Org. Lett., 2003, 5(23), 4417
[23] Kim H. Y., Lurain A. E., Garcia-Garcia P., Carroll P. J., Walsh P. J., J. Am. Chem. Soc., 2005, 127(38), 13138
[24] Son J. B., Hwang M. H., Lee W., Lee D. H., Org. Lett., 2007, 9(20), 3897
[25] Davoren J. E., Martin S. F., J. Am. Chem. Soc., 2007, 129(3), 510
[26] Qian D., Hu H., Liu F., Tang B., Ye W., Wang Y., Zhang J., Angew. Chem., Int. Ed., 2014, 53(50), 13751
[27] Qian D., Zhang J., Chem. Commun., 2011, 47(39), 11152
[28] Pohlman M., Kazmaier U., Org. Lett., 2003, 5(15), 2631
[29] Huang K., Huang Z. Z., Synlett., 2005, (10), 1621
[30] Zheng J. C., Liao W. W., Tang Y., Sun X. L., Dai L.X., J. Am. Chem. Soc., 2005, 127(35), 12222
[31] Aggarwal V. K., Grange E., Chem. Eur. J., 2006, 12(2), 568
[32] Kawai D., Kawasumi K., Miyahara T., Hirashita T., Araki S., Tetrahedron, 2009, 65(50), 10390
[33] Gololobov Y. G., Nesmeyanov A. N., Lysenko V. P., Boldeskul I. E., Tetrahedron, 1987, 43(12), 2609
[34] Padwa A., Ku H., J. Org. Chem., 1980, 45(19), 3756
[35] Zhang Y. B., An Y., Sun J., Ding A. S., Wang Y., Rios R. Guo H., Tetrahedron Lett., 2015, 56(46), 6499
[36] Zhang Y. B., Qian R., Zheng X. L., Zeng Y., Sun J., Chen Y. Y., Ding A. S., Guo H., Chem. Commun., 2015, 51(1), 54
[37] Kuang Y. L., Shen B., Dai L., Yao Q., Liu X. H., Lin L. L., Feng X. M., Chem. Sci., 2018, 9(3), 688
[38] Chen Z. G., Xia W., Liu D., Liu Y. L., Du M. F., Cao C. X., J. Chin. Chem. Soc., 2016, 63(2), 158
[39] Chen Z. G., Liu Y. L., Hu J. L., Liu D., Chem. Res. Chinese Universities, 2015, 31(1), 65
[40] Chen Z. G., Li Y. N., Zhou J. M., Wang D., Ge M., Chem. Res. Chinese Universities, 2014, 30(2), 266
[41] Chen Z. G., Wen H., Li W. L., Zhou J. M., Hu J. L., Xia W., J. Hetero. Chem., 2014, 51(3), 794
[42] Chen Z. G., Wei J. F., Wang M. Z., Zhou L. Y., Zhang C. J., Shi X. Y., Adv. Synth. Catal., 2009, 351(14/15), 2358
[43] Sun Q., Shi L. X., Ge Z. M., Cheng T. M., Li R. T., Chin. J. Chem., 2005, 23(6), 745
[44] Tu S. J., Rong L. C., Gao Y., Guo S. M., Lu S. H., Yang X. J., Chin. J. Org. Chem., 2002, 22(5), 364
[45] Giovannitti A., Seifermann S. M., Bihlmeier A., Muller T., Topic F., Rissanen K., Nieger M., Klopper W., Brase S., Eur. J. Org. Chem., 2013, (35), 7907
[46] Pravst I., Zupan M., Stavber S., Green Chem., 2006, 8(11), 1001

K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	JIANG Chang-sheng, LI You-gui, JIANG Chen, WEN Ji-wu, YOU Tian-pa. Asymmetric Cyclopropanation Catalyzed by a Copper-(Schiff-base)Complex with Double Chiral Centers [J]. Chemical Research in Chinese Universities, 2003, 19(2): 238-239.
[2]	ZHANG X. A., Campbell M. M., Brown, D. W. . Synthetic Studies on 1-Amino-1-Cyclopropane-Carboxylic Acid(Ⅰ)--The Cyclopropanation via Addition-Elimination Reactions [J]. Chemical Research in Chinese Universities, 1992, 8(4): 377-381.