Abstract
An efficient and facile procedure for the odourless and highly regioselective synthesis of β-hydroxyselenides by the ring-opening of epoxides with 1,2-diphenyldiselenide in the presence of Rongalite® and K2CO3 under solvent-free conditions on grinding has been developed. The important features of this methodology are high yields, reasonably rapid reaction rate, simple workup, high regioselectivity and no requirement for metal catalysts.
References
1.
Back T.G.
, ed. Organoselenium chemistry: a practical approach , Oxford University Press : Oxford , 1999 .
2.
Braga A.L.
,
Lüdtke D.S.
,
Vargas F.
, and
Braga R.C.
, Synlett , 2006 , 1453 .
3.
Braga A.L.
,
Lüdtke D.S.
,
Sehnem J.A.
, and
Alberto E.E.
, Tetrahedron , 2005 , 61 , 11664 .
4.
Nogueira C.W.
,
Zeni G.
,
Rocha J.B.T.
, Chem. Rev. , 2004 , 104 , 6255 .
5.
Back T.G.
, and
Moussa Z.
, J. Am. Chem. Soc. , 2003 , 125 , 13455 .
6.
Mugesh G.
,
du Mont W.W.
, and
Sies H.
, Chem. Rev. , 2001 , 101 , 2125 .
7.
Krief A.
, Tetrahedron , 1980 , 36 , 2531 .
8.
Sharpless K.B.
, and
Lauer R.F.
, J. Am. Chem. Soc. , 1973 , 95 , 2697 .
9.
Berlin S.
,
Ericsson C.
, and
Engman L.
, Org. Lett. , 2002 , 4 , 3 .
10.
Berlin S.
,
Ericsson C.
, and
Engman L.
, J. Org. Chem. , 2003 , 68 , 8386 .
11.
Tiecco M.
,
Testaferri L.
,
Santi C.
,
Tomassini C.
,
Marini F.
,
Bagnoli L.
, and
Temperini A.
, Angew. Chem., Int. Ed. , 2003 , 42 , 3131 .
12.
Yang M.H.
,
Yuan C.Y.
,
Pan Y.
, and
Zhu C.J.
, Chin. J. Chem. , 2006 , 24 , 669 .
13.
Das B.
,
Reddy V.S.
, and
Ramu R.
, J. Mol. Catal. A: Chem. , 2007 , 263 , 276 .
14.
Sridhar R.
,
Srinivas B.
,
Surendra K.
,
Krishnaveni N.S.
, and
Rao K.R.
, Tetrahedron Lett. , 2005 , 46 , 8837 .
15.
Yang M.H.
,
Yan G.B.
, and
Zheng Y.F.
, Tetrahedron Lett. , 2008 , 49 , 6471 .
16.
Kamal A.
,
Reddy D.R.
, and
Rajendar
, Tetrahedron Lett. , 2005 , 46 , 7951 .
17.
Zhang Y.M.
, and
Wang F.R.
, J. Chem. Res. (S ), 1998 , 598 .
18.
Jennifer D.
,
Fiona M.
, and
David J.P.
, Tetrahedron Lett. , 2000 , 41 , 4923 .
19.
Wang J.X.
,
Xi Y.
, and
Hu Y.
, J. Chem. Res. (S ), 2000 , 558 .
20.
Wang J.X.
,
Xi Y.
,
Hu Y.
,
Du Z.
, and
Zhao K.
, Synth. Commun. , 2000 , 30 , 2661 .
21.
Devan N.
,
Sridhar P.R.
,
Prabhu K.R.
, and
Chandrasekaran S.
, J. Org. Chem. , 2002 , 67 , 9417 .
22.
Barros O.S.R.
,
Carvalho A.B.
,
Lang E.S.
, and
Peppe C.
, Lett. Org. Chem. , 2004 , 1 , 43 .
23.
Chen X.A.
,
Wu H.Y.
,
Su W.K.
,
Xu R.
,
Liu M.C.
, and
Ding J.C.
, J. Chem. Res. (S ), 2007 , 325 .
24.
Zhang W.X.
,
Ye K.
,
Ruan S.
,
Chen Z.X.
, and
Xia Q.H.
, Chin. J. Chem. , 2007 , 25 , 1758 .
25.
Movassagh B.
, and
Shamsipoor M.
, Synlett , 2005 , 1316 .
26.
Santi C.
,
Santoro S.
,
Testaferri L.
, and
Tiecco M.
, Synlett , 2008 , 1471 .
27.
Ganesh V.
, and
Chandrasekaran S.
, Synthesis , 2009 , 3267 .
28.
Nishiyama Y.
,
Ohashi H.
,
Itoh K.
, and
Sonoda N.
, Chem. Lett. , 1998 , 159 .
29.
Santi C.
,
Santoro S.
,
Battistelli B.
,
Testaferri L.
, and
Tiecco M.
, Eur. J. Org. Chem. , 2008 , 5387 .
30.
Tiecco M.
,
Testaferri L.
,
Temperini A.
,
Bagnoli L.
,
Marini F.
, and
Santi C.
, Synlett , 2001 , 1767 .
31.
Zhang W.X.
,
Yu H.T.
,
Gao Y.
,
Meng J.B.
, and
Matsuura T.
, Chem. Commun. , 2003 , 498 .
32.
Guo W.X.
,
Chen J.X.
,
Wu D.Z.
,
Ding J.C.
,
Chen F.
, and
Wu H.Y.
, Tetrahedron , 2009 , 65 , 5240 .
33.
Guo W.X.
,
Lv G.S.
,
Chen J.X.
,
Gao W.X.
,
Ding J.C.
, and
Wu H.Y.
, Tetrahedron , 2010 , 66 , 2297 .
34.
William R.D.
,
Maurice M.
, and
Samia A.M.
, Tetrahedron Lett. , 2001 , 42 , 4811 .
35.
Huang B.N.
,
Liu J.T.
, and
Huang W. Y.
, J. Chem. Soc., Perkin Trans. 1 , 1994 , 101 .
36.
Hodgson W.G.
,
Neaves A.
, and
Parl C.A.
, Nature (London ), 1956 , 178 , 489 .
37.
Huang B.N.
, and
Liu J.T.
, Tetrahedron Lett. , 1990 , 31 , 2711 .
38.
Huang B.N.
,
Liu J.T.
, and
Huang W. Y.
, J. Chem. Soc., Chem. Commun. , 1990 , 1781 .
39.
Anselmi E.
,
Blazejewski J.C.
,
Tordeux M.
, and
Wakselman C.
, J. Fluorine Chem. , 2000 , 105 , 41
40.
Wu F.H.
,
Huang B.N.
,
Lu L.
, and
Huang W.Y.
, J. Fluorine Chem. , 1996 , 80 , 91 .
41.
Gruttadauria M.
,
Meo P.L.
,
Riela S.
,
D'Anna F.
, and
Noto R.
, Tetrahedron: Asymmetry , 2006 , 17 , 2713 .
