Abstract
A versatile and operationally simple base-catalyzed multi-component domino reaction
between α,β-unsaturated carbonyl compounds, aldehydes, and alcohols is described,
providing a new efficient, and stereoselective one-pot preparation of trisubstituted
alkenes and 1,3-dienes.
Key words
multi-component domino reaction - one-pot synthesis - trisubstituted alkenes - 1,3-dienes
References
<A NAME="RP01705SS-1">1 </A>
The Chemistry of Alkenes
Patai S.
Interscience;
New York:
1968.
<A NAME="RP01705SS-2">2 </A>
Williams JMJ.
Preparation of Alkenes: A Practical Approach
Oxford University Press;
Oxford, U.K.:
1996.
<A NAME="RP01705SS-3">3 </A>
Shen Y.
Acc. Chem. Res.
1998,
31:
584
<A NAME="RP01705SS-4">4 </A>
Nakatsu S.
Gubaidullin AT.
Mamedov VA.
Tsuboi S.
Tetrahedron
2004,
60:
2337
<A NAME="RP01705SS-5">5 </A>
Astles PC.
Mortlock SF.
Thoma EJ. In
Comprehensive Organic Synthesis
Vol. 6:
Trost BM.
Fleming I.
Pergamon Press;
Oxford:
1991.
p.1011
<A NAME="RP01705SS-6">6 </A>
Ouvry G.
Quiclet-Sire B.
Zard SZ.
Org. Lett.
2003,
5:
2907
<A NAME="RP01705SS-7">7 </A>
Salaun J.
Fadel A.
Org. Synth.
1986,
64:
50
<A NAME="RP01705SS-8">8 </A>
Franklin AS.
J. Chem. Soc., Perkin Trans. 1
1998,
2451
<A NAME="RP01705SS-9">9 </A>
Maryanoff BE.
Reitz AB.
Chem. Rev.
1989,
89:
863
<A NAME="RP01705SS-10">10 </A>
Castells J.
Lopez-Calahorra F.
Yu Z.
Tetrahedron
1994,
50:
13765
<A NAME="RP01705SS-11">11 </A>
van Staden LF.
Gravestock D.
Ager DJ.
Chem. Soc. Rev.
2002,
31:
195
<A NAME="RP01705SS-12">12 </A>
Blakemore PR.
J. Chem. Soc., Perkin Trans. 1
2002,
2563
<A NAME="RP01705SS-13">13 </A>
Fan R.-H.
Hou X.-L.
Dai L.-X.
J. Org. Chem.
2004,
69:
689
<A NAME="RP01705SS-14">14 </A>
Yoshida M.
Gotou T.
Ihara M.
Chem. Commun.
2004,
1124
<A NAME="RP01705SS-15">15 </A>
Nair V.
Devi BR.
Vidya N.
Menon RS.
Abhilash N.
Rath NP.
Tetrahedron Lett.
2004,
45:
3203
<A NAME="RP01705SS-16">16 </A>
Ballini R.
Barboni L.
Bosica G.
Fiorini D.
Mignini E.
Palmieri A.
Tetrahedron
2004,
60:
4995
<A NAME="RP01705SS-17">17 </A>
Barma DK.
Kundu A.
Zhang H.
Mioskowski C.
Falck JR.
J. Am. Chem. Soc.
2003,
125:
3218
<A NAME="RP01705SS-18">18 </A>
Concellon JM.
Rodriguez-Solla H.
Mejica C.
Tetrahedron Lett.
2004,
45:
2977
<A NAME="RP01705SS-19">19 </A>
Gurtler C.
Buchwald SL.
Chem.-Eur. J.
1999,
5:
3107
<A NAME="RP01705SS-20">20 </A>
Zhang X.
Qing F.-L.
Yu Y.
J. Org. Chem.
2000,
65:
7075
<A NAME="RP01705SS-21">21 </A>
Tanaka K.
Katsumura S.
Org. Lett.
2000,
2:
373
<A NAME="RP01705SS-22">22 </A>
Qing F.-L.
Zhang X.
Tetrahedron Lett.
2001,
42:
5929
<A NAME="RP01705SS-23">23 </A>
Basavaiah D.
Rao AJ.
Satyanarayana T.
Chem. Rev.
2003,
103:
811
<A NAME="RP01705SS-24">24 </A>
Burk MJ.
De Koning PD.
Grote TM.
Hoekstra MS.
Hoge G.
Jennings RA.
Kissel WS.
Le TV.
Lennon IC.
Mulhern TA.
Ramsden JA.
Wade RA.
J. Org. Chem.
2003,
68:
5731
<A NAME="RP01705SS-25">25 </A>
Das B.
Banerjee J.
Ravindranath N.
Venkataiah B.
Tetrahedron Lett.
2004,
45:
2425
<A NAME="RP01705SS-26">26 </A>
Navarre L.
Darses S.
Genet J.-P.
Chem. Commun.
2004,
1108
<A NAME="RP01705SS-27">27 </A>
Basavaiah D.
Rao JS.
Tetrahedron Lett.
2004,
45:
1621
<A NAME="RP01705SS-28">28 </A>
Ramachandran PV.
Pratihar D.
Biswas D.
Srivastava A.
Reddy MVR.
Org. Lett.
2004,
6:
481
<A NAME="RP01705SS-29">29 </A>
Mamaghani M.
Badrian A.
Tetrahedron Lett.
2004,
45:
1547
<A NAME="RP01705SS-30">30 </A>
Kotti SRSS.
Xu X.
Li G.
Headley AD.
Tetrahedron Lett.
2004,
45:
1427
<A NAME="RP01705SS-31">31 </A>
Charonnet E.
Filippini M.-H.
Rodriguez J.
Synthesis
2001,
788
<A NAME="RP01705SS-32">32 </A>
Simon C.
Peyronel J.-F.
Rodriguez J.
Org. Lett.
2001,
3:
2145
<A NAME="RP01705SS-33">33 </A>
Habib-Zahmani H.
Hacini S.
Charonnet E.
Rodriguez J.
Synlett
2002,
1827
<A NAME="RP01705SS-34">34 </A>
Simon C.
Lieby-muller F.
Peyronel J.-F.
Constantieux T.
Rodriguez J.
Synlett
2003,
2301
<A NAME="RP01705SS-35">35 </A>
Simon C.
Constantieux T.
Rodriguez J.
Eur. J. Org. Chem.
2004,
4957
<A NAME="RP01705SS-36">36 </A>
Buchanan DJ.
Dixon DJ.
Hernandez-Juan FA.
Org. Lett.
2004,
6:
1357
<A NAME="RP01705SS-37">37 </A>
Greatrex BW.
Kimber MC.
Taylor DK.
Tiekink ERT.
J. Org. Chem.
2003,
68:
4239
<A NAME="RP01705SS-38">38 </A>
Ciganek E.
J. Org. Chem.
1995,
60:
4635
<A NAME="RP01705SS-39">39 </A>
Lesch B.
Braese S.
Angew. Chem. Int. Ed.
2004,
43:
115
<A NAME="RP01705SS-40">40 </A>
Kaye PT.
Nocanda XW.
J. Chem. Soc., Perkin Trans. 1
2002,
1318
<A NAME="RP01705SS-41">41 </A>
Fernandez de la Pradilla R.
Tortosa M.
Org. Lett.
2004,
6:
2157
