Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones

doi:10.1007/s40242-014-4061-7

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (4): 596-600.doi: 10.1007/s40242-014-4061-7

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Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones

CAO Long¹, ZHOU Xiaohong¹, CHEN Jie¹, ZHANG Hui³, DENG Hongmei³, SHAO Min³, McMILLS Mark C.⁴, CAO Weiguo^1,2

1. Department of Chemistry, Shanghai University, Shanghai 200444, P. R. China;
2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China;
3. Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. China;
4. Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA

Online:2014-08-01 Published:2014-05-12
Contact: McMILLS Mark C, CAO Weiguo E-mail:wgcao@staff.shu.edu.cn;mcmills@ohio.edu
Supported by:
Supported by the National Natural Science Foundation of China(No.21272152).

Abstract

Abstract:

Trans-2,3-dihydrofuran derivatives 3 or 4 substituted with a sulfonyl group were prepared with high chemoselectivity and good yields by [1+4]-addition reaction of α,β-unsaturated ketones 1 with arsonium bromide 2 in CH₂Cl₂ in the presence of potassium carbonate at room temperature. The structures of the products were characterized by IR, MS, ¹H NMR, elemental analysis and single crystal X-ray diffraction analysis. A mechanism for the formation of products was also proposed.

Key words: Stereoselectivity, Dihydrofuran, Arsonium Ylide

CAO Long, ZHOU Xiaohong, CHEN Jie, ZHANG Hui, DENG Hongmei, SHAO Min, McMILLS Mark C., CAO Weiguo. Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones[J]. Chemical Research in Chinese Universities, 2014, 30(4): 596-600.

References

[1] Fraga B. M., Nat. Prod. Rep., 1992, 9, 217
[2] Merritt A. T., Ley S. V., Nat. Prod. Rep., 1992, 9, 243
[3] Schoop A., Greiving H., Gohrt A., Tetrahedron Lett., 2000, 41, 1913
[4] Schabbert S., Schaumann E., Eur. J. Org. Chem., 1998, 1873
[5] Ruano G. J. L., Bercial F., González G., Castro A. M. M., Martín M. R., Tetrahedron: Asymmetry, 2002, 13, 1993
[6] Ruano G. J. L., Bercial F., Fraile A., Castro A. M. M., Martín M. R., Tetrahedron: Asymmetry, 2000, 11, 4737
[7] Zhang Y., Raines A. J., Flowers R. A., Org. Lett., 2003, 5, 2363
[8] Evans D. A., Sweeney Z. K., Rovis T., Tedrow J. S., J. Am. Chem. Soc., 2001, 123, 12095
[9] Hamaguchi M., Matsubara H., Nagai T., J. Org. Chem., 2001, 66, 5395
[10] Antonioletti R., Righi G., Oliveri L., Bovicelli P., Tetrahedron Lett., 2000, 41, 10127
[11] Hagiwara H. S. K., Suzuki T., Ando M., Tetrahedron Lett., 1997, 38, 2103
[12] Gais H. J., Reddy L. R., Babu G. S., Raabe G., J. Am. Chem. Soc., 2004, 126, 4859
[13] Xing C., Zhu S., J. Org. Chem., 2004, 69, 6486
[14] Arai S., Nakayama K., Suzuki Y., Hatano K., Shioiri T., Tetrahedron Lett., 1998, 39, 9739
[15] Lee Y. R., Yoon S. H., Seo Y., Kim B. S., Synthesis, 2004, 17, 2787
[16] Lee J. W., Dong Y., Heterocycles, 1990, 31, 1417
[17] Feldman K. S., Wrobleski M. L., J. Org. Chem., 2000, 65, 8659
[18] Moorhoff C. M., Tetrahedron Lett., 1996, 37, 9349
[19] Ding W., Tong W., Zhai Y., Cai Z., Chem. J. Chinese Universities, 1999, 21(1), 64
[20] Cao W., Ding W., Chen J., Zang Q., Chen G., Synth. Commun., 2004, 34, 1599
[21] Chen G., Cao W., Chen J., Chen R., Synth. Commun., 2004, 34, 3793
[22] Cao W., Chen G., Chen J., Chen R., Synth. Commun., 2005, 35, 527
[23] Qian J., Cao W., Zhang H., Chen J., Zhu, S., J. Fluorine Chem., 2007, 128, 207
[24] Zhang H., Cao W., Chen J., Hu J., Qian J., Zhu S., Chin. J. Chem., 2007, 25, 968
[25] Cao W., Zhang H., Chen J., Zhou X., Shao M., McMills M. C., Tetrahedron, 2008, 64, 163
[26] Yu H., Han J., Chen J., Deng H., Shao M., Zhang H., Cao W., Eur. J. Org. Chem., 2012, 16, 3142
[27] Yang Z., Fan M., Mu R., Liu W., Liang Y., Tetrahedron, 2005, 61, 9140
[28] Yang Z., Fan M., Liu W., Liang Y., Synthesis, 2005, 13, 2188
[29] Cao W., Ding W., Ding W., Huang H., J. Fluorine Chem., 1997, 83, 21

Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones

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