Stereoselective synthesis of sulfonyl-substituted trans-2,3-dihydrofuran derivatives via reaction of arsonium Ylides with α,β-unsaturated ketones

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.

Keywords

Stereoselectivity / Dihydrofuran / Arsonium Ylide

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.