Abstract
Ultrasound assisted ring-opening of epoxides with 1,2-diphenyldiselenide in PEG-400/H2O in the presence of sodium dithionite has been developed, affording β-hydroxy selenides with high regioselectivity in good to excellent yields. Importantly, the present protocol is very practical and highly efficient since it does not require the use of expensive and unpleasant smelly reagent.
References
1.
Krief A.
, Tetrahedron , 1980 , 36 , 2531 .
2.
Sharpless K.B.
, and
Lauer R.F.
, J. Am. Chem. Soc. , 1973 , 95 , 2697 .
3.
Berlin S.
,
Ericsson C.
, and
Engman L.
, J. Org. Chem. , 2003 , 68 , 8386 .
4.
Yang M.H.
,
Yuan C.Y.
,
Pan Y.
, and
Zhu C.J.
, Chin. J. Chem. , 2006 , 24 , 669 .
5.
Das B.
,
Reddy V.S.
, and
Ramu R.
, J. Mol. Catal. A: Chem. , 2007 , 263 , 276 .
6.
Sridhar R.
,
Srinivas B.
,
Surendra K.
,
Krishnaveni N.S.
, and
Rao K.R.
, Tetrahedron Lett. , 2005 , 46 , 8837 .
7.
Yang M.H.
,
Yan G.B.
, and
Zheng Y.F.
, Tetrahedron Lett. , 2008 , 49 , 6471 .
8.
Zhang Y.M.
, and
Wang F.R.
, J. Chem. Res. , 1998 , 598 .
9.
Jennifer D.
,
Fiona M.
, and
David J.P.
, Tetrahedron Lett. , 2000 , 41 , 4923 .
10.
Wang J.X.
,
Xi Y.
, and
Hu Y.
, J. Chem. Res. , 2000 , 558 .
11.
Devan N.
,
Sridhar P.R.
,
Prabhu K.R.
, and
Chandrasekaran S.
, J. Org. Chem. , 2002 , 67 , 9417 .
12.
Barros O.S.R.
,
Carvalho A.B.
,
Lang E.S.
, and
Peppe C.
, Lett. Org. Chem. , 2004 , 1 , 43 .
13.
Chen X.A.
,
Wu H.Y.
,
Su W.K.
,
Xu R.
,
Liu M.C.
, and
Ding J.C.
, J. Chem. Res. , 2007 , 31 , 325 .
14.
Zhang W.X.
,
Ye K.
,
Ruan S.
,
Chen Z.X.
, and
Xia Q.H.
, Chin. J. Chem. , 2007 , 25 , 1758 .
15.
Sakakibara M.
,
Katsumata K.
,
Watanabe Y.
,
Toru T.
, and
Ueno Y.
, Synthesis , 1992 , 377 .
16.
Movassagh B.
, and
Shamsipoor M.
, Synlett , 2005 , 1316 .
17.
Santi C.
,
Santoro S.
,
Testaferri L.
, and
Tiecco M.
, Synlett , 2008 , 1471 .
18.
Lv G.S.
,
Li T.
,
Hu R.J.
,
Chen J.X.
,
Ding J.C.
, and
Wu H.Y.
, J. Chem. Res. , 2010 , 34 , 549 .
19.
Cravotto G.
, and
Cintas P.
, Angew. Chem. Int. Ed. , 2007 , 46 , 5476 .
20.
Koda S.
,
Kimurab T.
,
Kondoc T.
, and
Mitomed H.
, Ultrason. Sonochem. , 2003 , 13 , 149 .
21.
Zhang Z.H.
,
Li J.J.
, and
Li T.S.
, Ultrason. Sonchem. , 2008 , 15 , 673 .
22.
Ge S.Q.
,
Hua Y.Y.
, and
Xia M.
, Ultrason. Sonochem. , 2009 , 16 , 743 .
23.
Ni C.L.
,
Song X.H.
,
Yan H.
,
Song X.Q.
, and
Zhong R.G.
, Ultrason. Sonochem. , 2010 , 17 , 367 .
24.
Zou Y.
,
Wu H.
,
Hu Y.
,
Liu H.
,
Zhao X.
,
Ji H.L.
, and
Shi D.Q.
, Ultrason. Sonochem. , 2011 , 18 , 708 .
25.
Dickerson T.J.
,
Reed N.N.
, and
Janda K.D.
, Chem. Rev. , 2002 , 102 , 3325 .
26.
Jain S.L.
,
Singhal S.
, and
Sain B.
, Green Chem. , 2007 , 9 , 740 .
27.
Smith C.B.
,
Raston C.L.
, and
Sobolev A.N.
, Green Chem. , 2005 , 7 , 650 .
28.
Chandrasekhar S.
,
Narsihmulu C.
,
Sultana S.S.
, and
Reddy N.R.
, Chem. Commun. , 2003 , 1716 .
29.
Jin H.L.
,
Cheng T.X.
, and
Chen J.X.
, Appl. Organometal. Chem. , 2011 , 25 , 238 .