Abstract
The Michael addition of active methylene compounds or nitromethane to chalcones in an aqueous medium and catalysed by tetrabutyl ammonium hydroxide (TBAOH) to afford highly substituted cyclohexanols is described. The protocol provides an efficient route for the synthesis of highly substituted cyclohexanols, with short reaction time, and a range of different substrates in the absence of toxic organic solvents.
References
1.
Mekonnen A.
, and
Carlson R.
, Eur. J. Org. Chem. , 2006 , 2005 .
2.
Yang H.M.
,
Gao Y.H.
,
Li L.
, and
Jiang Z.Y.
, Tetrahedron Lett. , 2010 , 51 , 3836 .
3.
Song W.Z.
,
Lu W.
,
Wang J.
,
Lu P.
, and
Wang Y.G.
, J. Org. Chem. , 2010 , 75 , 3481 .
4.
Tsogoeva S.B.
, Eur. J. Org. Chem. , 2007 , 1701 .
5.
Fatma E.G.
,
Alaa A.M.
,
Abdel A.
, and
Omer A.A.
, Bioorg. Med. Chem. , 2004 , 12 , 1845 .
6.
Lu Y.D.
, and
Arndtsen B.A.
, Org. Lett. , 2009 , 11 , 1369 .
7.
Wang G.W.
,
Zhuang L.H.
, and
Wang J.T.
, J. Chem. Res. , 2009 , 212 .
8.
Wei T.B.
,
Hua M.T.
,
Shi H.X.
,
Liu Y.
, and
Zhang Y.M.
, J. Chem. Res. , 2010 , 34 , 452 .
9.
Liu P.N.
,
Dang L.
,
Wang Q.W.
, and
Zhao S.J.
, J. Org. Chem. , 2010 , 75 , 5017 .
10.
Liu P.N.
,
Xia F.
,
Wang Q.W.
,
Ren Y.J.
, and
Chen J.Q.
, Green Chem. , 2010 , 12 , 1049 .
11.
Minakata S.
, and
Komatsu M.
, Chem. Rev. , 2009 , 109 , 711 .
12.
Li C.J.
, Chem. Rev. , 2005 , 105 , 3095 .
13.
Chanda A.
, and
Fokin V.V.
, Chem. Rev. , 2009 , 109 , 725 .
14.
Charles M.S.
, Phase-transfer catalysis , American Chemical Society , 1987 , pp. 1 –7 .
15.
Yang H.M.
, and
Li C.C.
, J. Mol. Catal. A: Chem. , 2006 , 246 , 255 .
16.
Lin P.J.
, and
Yang H.M.
, J. Mol. Catal. A: Chem. , 2005 , 235 , 293 .
17.
Lindstrom U.M.
, Chem. Rev. , 2002 , 102 , 2751 .
18.
Babu T.H.
,
Karthik K.
, and
Perumal P.T.
, Synlett , 2010 , 1128 .
19.
Arab A.
,
Mohammad M.
,
Tabba H.D.
,
Ghanem B.S.
, and
Olmstead M.M.
, Synthesis , 1990 , 1157 .
20.
Victory P.
,
Borrell J.I.
,
Vidal F.A.
,
Seoane C.
, and
Soto J.L.
, Tetrahedron Lett. , 1991 , 32 , 5375 .
21.
Jin T.S.
,
Yin Y.
,
Liu L.B.
,
Zhao Y.
, and
Li T.S.
, Chin. J. Org. Chem. , 2007 , 27 , 261 .
22.
Correc O.
,
Guillou K.
,
Hamelin J.
,
Paquin L.
,
Texier-Boullet F.
, and
Toupet L.
, Tetrahedron Lett. , 2004 , 45 , 391 .
23.
Wang A.Q.
,
Jin T.S.
,
Liu L.B.
,
Cheng Z.L.
, and
Li T.S.
, Asian J. Chem. , 2010 , 22 , 1977 .
24.
Slätt J.
,
Romero I.
, and
Bergman J.
, Synthesis , 2004 , 2760 .
25.
Thirumurugan P.
, and
Perumal P.T.
, Tetrahedron , 2009 , 65 , 7620 .
26.
Li Z.X.
, and
Li A.L.
, J. Chin. Pharm. Sci. , 2004 , 13 , 245 .
