Abstract
The reactivity of in situ generated organozinc reagents of 3-alkenyl-3-bromoazetidin-2-ones
with aromatic and aliphatic aldehydes to give the corresponding alcohol derivatives
has been studied. The effect of solvent and Lewis acids has been explored in order
to improve the reaction yields. The application of this methodology to nitriles and
acyl chlorides allowed the preparation of the corresponding keto derivatives. The
products of these reactions could be of interest on account of their structural similarity
with the already known cholesterol adsorption inhibitors.
Key words
zinc - aldehydes - condensation - azetidinones - allylic organozinc reagents - Lewis
acids
References
<A NAME="RZ15104SS-1A">1a</A>
Knochel P.
Millot N.
Rodriguez AL.
Tucker CE.
Org. React.
2001,
58:
417
<A NAME="RZ15104SS-1B">1b</A>
Knochel P.
Singer RD.
Chem. Rev.
1993,
93:
2117
<A NAME="RZ15104SS-2A">2a</A>
Masuyama Y.
Rec. Res. Dev. Org. Chem.
2000,
4:
373
<A NAME="RZ15104SS-2B">2b</A>
Luche J.-L.
Sarandeses LA. In
Organozinc Reagents - A Practical Approach
Knochel P.
Jones P.
Oxford University Press;
Oxford:
1999.
p.307-323
<A NAME="RZ15104SS-2C">2c</A>
Alonso F.
Yus M.
Rec. Res. Dev. Org. Chem.
1997,
1:
397
<A NAME="RZ15104SS-2D">2d</A>
Tagliavini E.
Trombini C.
Umani-Ronchi A. In
Advances in Carbanion Chemistry
Vol. 2:
Snieckus V.
Jai Press Inc;
Greenwich:
1996.
p.111-146
<A NAME="RZ15104SS-2E">2e</A>
Rathke MK.
Weipert P. In
Comprehensive Organic Synthesis
Vol. 2:
Trost BM.
Pergamon;
Oxford:
1991.
p.277-299
<A NAME="RZ15104SS-2F">2f</A>
Fürstner A.
Synthesis
1989,
571
<A NAME="RZ15104SS-2G">2g</A>
Heathcock CH. In
Asymmetric Synthesis
Vol. 3:
Morrison JD.
Academic Press;
New York:
1984.
p.144-152
<A NAME="RZ15104SS-3A">3a</A>
Clader J.
Science
2004,
303:
1201
<A NAME="RZ15104SS-3B">3b</A>
Singh GS.
Mini Rev. Med. Chem.
2004,
4:
69
<A NAME="RZ15104SS-3C">3c</A>
Wu GG.
Org. Process Res. Dev.
2000,
4:
298
<A NAME="RZ15104SS-3D">3d</A>
McKittrick BA.
Ma K.
Huie K.
Yumibe N.
Davis H.
Clader JW.
Czarniecki M.
McPhail AT.
J. Med. Chem.
1998,
41:
752
<A NAME="RZ15104SS-3E">3e</A>
Burnett DA.
Caplen MA.
Davis H.
Burrier RE.
Clader JW.
J. Med. Chem.
1994,
37:
1733
<A NAME="RZ15104SS-4A">4a</A>
Alcaide B.
Almendros P.
Aragoncillo C.
Rodriguez-Acebes R.
J. Org. Chem.
2004,
69:
826
<A NAME="RZ15104SS-4B">4b</A>
Alcaide B.
Almendros P.
Aragoncillo C.
Rodriguez-Acebes R.
Synthesis
2003,
1163
<A NAME="RZ15104SS-4C">4c</A>
Alcaide B.
Almendros P.
Aragoncillo C.
Rodriguez-Acebes R.
J. Org. Chem.
2001,
66:
5208
<A NAME="RZ15104SS-4D">4d</A>
Paquette LA.
Rothhaar RR.
Isaac M.
Rogers LM.
Rogers RD.
J. Org. Chem.
1998,
63:
5463
<A NAME="RZ15104SS-4E">4e</A>
Jayaraman M.
Batista MT.
Manhas MS.
Bose AK.
Heterocycles
1998,
49:
97
<A NAME="RZ15104SS-4F">4f</A>
Jayaraman M.
Manhas MS.
Bose AK.
Tetrahedron Lett.
1997,
38:
709
<A NAME="RZ15104SS-4G">4g</A>
Palomo C.
Aizpurua JM.
Lopez MC.
Aurrekoetxea N.
Oiarbide M.
Tetrahedron Lett.
1990,
31:
6425
<A NAME="RZ15104SS-5">5</A>
Palomo C.
Aizpurua JM.
Ganboa I.
Oiarbide M.
Eur. J. Org. Chem.
1999,
3223
<A NAME="RZ15104SS-6A">6a</A>
Cardillo G.
Fabbroni S.
Gentilucci L.
Perciaccante R.
Piccinelli F.
Tolomelli A.
Tetrahedron
2004,
60:
5031
<A NAME="RZ15104SS-6B">6b</A>
Cardillo G.
Fabbroni S.
Gentilucci L.
Perciaccante R.
Tolomelli A.
Tetrahedron: Asymmetry
2004,
15:
593
<A NAME="RZ15104SS-6C">6c</A>
Cardillo G.
De Simone A.
Mingardi A.
Tomasini C.
Synlett
1995,
1131
<A NAME="RZ15104SS-7A">7a</A>
Manhas MS.
Banik BK.
Mathur A.
Vincent JE.
Bose AK.
Tetrahedron
2000,
56:
5587
<A NAME="RZ15104SS-7B">7b</A>
Manhas MS.
Ghosh M.
Bose AK.
J. Org. Chem.
1990,
55:
575
<A NAME="RZ15104SS-7C">7c</A>
Zamboni R.
Just G.
Can. J. Chem.
1979,
57:
1945
<A NAME="RZ15104SS-7D">7d</A>
Bose AK.
Spiegelmann G.
Manhas MS.
Tetrahedron Lett.
1971,
3167
<A NAME="RZ15104SS-8A">8a</A>
Bari SS.
Venugopalan P.
Arora R.
Tetrahedron Lett.
2003,
44:
895
<A NAME="RZ15104SS-8B">8b</A>
Kingston DGI.
Chem. Commun.
2001,
867
<A NAME="RZ15104SS-8C">8c</A>
Bandini E.
Favi G.
Martelli G.
Panunzio M.
Piersanti G.
Org. Lett.
2000,
2:
1077
<A NAME="RZ15104SS-8D">8d</A>
Kende AS.
Liu K.
Kaldor I.
Dorey G.
Koch K.
J. Am. Chem. Soc.
1995,
117:
8258
<A NAME="RZ15104SS-8E">8e</A>
Nicolaou KC.
Doi WM.
Guy RK.
Angew. Chem., Int. Ed. Engl.
1994,
33:
15
<A NAME="RZ15104SS-8F">8f</A>
Ojima I.
Habus I.
Zhao M.
Zucco M.
Park YH.
Sun CM.
Brigaud T.
Tetrahedron
1992,
48:
6985
<A NAME="RZ15104SS-8G">8g</A>
Duran F.
G hosez L.
Tetrahedron Lett.
1970,
11:
245
<A NAME="RZ15104SS-9">9</A>
The reactions were performed on racemic mixtures. For the sake of simplicity only
one enantiomer has been reported in the schemes.
<A NAME="RZ15104SS-10A">10a</A>
Freihammer PM.
Detty MR.
J. Org. Chem.
2000,
65:
7203
<A NAME="RZ15104SS-10B">10b</A>
Durst T.
Sharma MK.
Gabe EJ.
Lee FL.
J. Org. Chem.
1990,
55:
5525
<A NAME="RZ15104SS-11">11</A>
Detailed X-ray data for 3a and 3b are reported in the experimental section. CCDC number for 3a is 245012, CCDC number for 3b is 245013.
<A NAME="RZ15104SS-12A">12a</A>
Lindstroem UM.
Chem. Rev.
2002,
102:
2751
<A NAME="RZ15104SS-12B">12b</A>
Kobayashi S.
Manabe K.
Acc. Chem. Res.
2002,
35:
209
<A NAME="RZ15104SS-12C">12c</A>
Fringuelli F.
Piermatti O.
Pizzo F.
Vaccaro L.
Eur. J. Org. Chem.
2001,
3:
439
<A NAME="RZ15104SS-12D">12d</A>
Dias LC.
Curr. Org. Chem.
2000,
4:
305
<A NAME="RZ15104SS-12E">12e</A>
Laszlo P.
Teston M.
J. Am. Chem. Soc.
1990,
112:
8750
<A NAME="RZ15104SS-13A">13a</A>
Kobayashi S.
Busujima T.
Nagayama S.
Chem. Eur. J.
2000,
6:
3491
<A NAME="RZ15104SS-13B">13b</A>
Ferraris D.
Drury WJ.
Cox C.
Lectka T.
J. Org. Chem.
1998,
63:
4568
<A NAME="RZ15104SS-13C">13c</A>
Pearson RG.
J. Am. Chem. Soc.
1963,
85:
3533
<A NAME="RZ15104SS-14A">14a</A>
Dilman AD.
Ioffe SL.
Chem. Rev.
2003,
103:
733
<A NAME="RZ15104SS-14B">14b</A>
Bongini A.
Cardillo G.
Mingardi A.
Tomasini C.
Tetrahedron: Asymmetry
1996,
7:
1457
<A NAME="RZ15104SS-14C">14c</A>
Lipshutz BH.
Dimock SH.
James B.
J. Am. Chem. Soc.
1993,
115:
9283
<A NAME="RZ15104SS-14D">14d</A>
Lipshutz BH.
James B.
Tetrahedron Lett.
1993,
34:
6689
<A NAME="RZ15104SS-15">15</A>
Cainelli G.
Cardillo G.
Orena M.
Sandri S.
J. Am. Chem. Soc.
1976,
98:
6737
<A NAME="RZ15104SS-16A">16a</A>
Iwai T.
Ito T.
Mizuno T.
Ishino Y.
Tetrahedron Lett.
2004,
45:
1083
<A NAME="RZ15104SS-16B">16b</A>
Lee AS.-Y.
Lin L.-S.
Tetrahedron Lett.
2000,
41:
8803
