Abstract
Under microwave-assisted solvent-free conditions a one-pot reaction of triphenylphosphine, an aldehyde and N, N-diethyl chloroacetamide in the presence of zinc dust affords α, β-unsaturated amides stereoselectively in good yield. In comparison with the conventional heating method, the reaction was finished within five minutes under microwave irradiation.
References
1.
Gedye R.
,
Smith F.
,
Westaway K.
,
Ali H.
,
Baldisera L.
,
Laberge L.
, and
Rousell J.
, Tetrahedron Lett. , 1986 , 27 , 297 .
2.
Giguere R.J.
,
Bray T. L.
,
Duncan S. M.
, and
Majetich G.
, Tetrahedron Lett. , 1986 , 27 , 4945 .
3.
Yu X.C.
, and
Huang X.
, Synlett , 2002 , 11 , 1895 .
4.
Wu J.L.
,
Wu H. F.
,
Wei S. Y.
, and
Dai W. M.
, Tetrahedron Lett. , 2004 , 45 , 4401 .
5.
Prokopcová H.
,
Ramírez J.
,
Fernández E.
, and
Kappe C. O.
, Tetrahedron Lett. , 2008 , 49 , 4831 .
6.
Caramella P.
,
Reami D.
,
Falzoni M.
, and
Quadrelli P.
, Tetrahedron , 1999 , 55 , 7027 .
7.
Cardillo G.
,
Hashem M. A.
, and
Tomasini C.
, J. Chem. Soc., Perkin Trans. , 1990 , 1 , 1587 .
8.
Gothelf R.F.
, and
Jorgensen K. A.
, Chem. Rev. , 1998 , 98 , 863 .
9.
Takai K.
,
Tezuka M.
, and
Utimoto K.
, J. Org. Chem. , 1991 , 56 , 5980 .
10.
Park J.H.
,
Kim S. Y.
,
Kim S. M.
, and
Chung Y. K.
, Org. Lett. , 2007 , 9 , 2465 .
11.
Wu X.Y.
,
Wannberg J.
, and
Larhed M.
, Tetrahedron , 2006 , 62 , 4665 .
12.
Wu X.Y.
,
Ekegren J. K.
, and
Larhed M.
, Organometallics , 2006 , 25 , 1434 .
13.
Muller E.
,
Peczely G.
,
Skoda-Foldes R.
,
Takacs E.
,
Kokotos G.
,
Bellis E.
, and
Kollar L.
, Tetrahedron , 2005 , 61 , 797 .
14.
Wannberg J.
, and
Larhed M.
, J. Org. Chem. , 2003 , 68 , 5750
15.
Takacs E.
,
Skoda-Foldes R.
,
Acs P.
,
Muller E.
,
Kokotos G.
, and
Kollar L.
, Lett. Org. Chem. , 2006 , 3 , 62 .
16.
Du J.X.
, and
Huang X.
, Chemical Journal of Chinese Universities , 1994 , 15 , 1481 .
17.
Concellón J.M.
, and
Bardales E.
J. Org. Chem. , 2003 , 68 , 9492
18.
Concellón J.M.
,
Pérez-Andrés J. A.
, and
Rodríguez-Solla H.
, Chem. Eur. J. , 2001 , 7 , 3062 .
19.
Concellón J.M.
,
Rodríguez-Solla H.
, and
Díaz P.
, J. Org. Chem. , 2007 , 72 , 7974 .
20.
Hernández-Fernández E.
,
Fernández-Zertuche M.
,
García-Barradas O.
,
Muñoz-Muñiz O.
, and
Ordoñez M.
, Synlett , 2006 , 440 .
21.
Kojima S.
,
Inai H.
,
Hidaka T.
,
Fukuzaki T.
, and
Ohkata K.
, J. Org. Chem. , 2002 , 67 , 4093 .
22.
Zheng J.H.
;
Wang Z. B.
, and
Shen Y. C.
, Synth. Commun. , 1992 , 22 , 1611 .
23.
Chevrie D.
,
Lequeux T.
, and
Pommelet J. C.
, Org. Lett. , 1999 , 1 , 1539 .
