Abstract
The conversion of β-keto esters into β-methylated γ-keto esters can be achieved through
treatment with zinc carbenoids derived from 1,1-diiodoethane. The incorporation of
a β-phenyl substituent is also possible through treatment with diiodotoluene.
Key Words
carbenoids - diiodoethane - esters - chain extension - zinc
References
<A NAME="RM05506SS-1A">1a </A>
Reissig H.-H.
Top. Curr. Chem.
1988,
144:
73
<A NAME="RM05506SS-1B">1b </A>
Bieraugel H.
Akkerman JM.
Lapierre Armond JC.
Pandit UK.
Tetrahedron Lett.
1974,
2817
<A NAME="RM05506SS-1C">1c </A>
Dowd P.
Choi S.-C.
J. Am. Chem. Soc.
1987,
109:
3493
<A NAME="RM05506SS-2A">2a </A>
Brogan JB.
Zercher CK.
J. Org. Chem.
1997,
62:
6444
<A NAME="RM05506SS-2B">2b </A>
Hilgenkamp R.
Zercher CK.
Tetrahedron
2001,
57:
8793
<A NAME="RM05506SS-2C">2c </A>
Verbicky CA.
Zercher CK.
J. Org. Chem.
2000,
65:
5615
<A NAME="RM05506SS-3">3 </A>
Lai S.-J.
Zercher CK.
Jasinski JP.
Reid SN.
Staples RJ.
Org. Lett.
2001,
3:
4169
<A NAME="RM05506SS-4">4 </A>
Hilgenkamp R.
Zercher CK.
Org. Lett.
2001,
3:
3037
<A NAME="RM05506SS-5">5 </A>
Pu, Q., unpublished results, University of New Hampshire.
<A NAME="RM05506SS-6">6 </A>
Ronsheim MD.
Zercher CK.
J. Org. Chem.
2003,
68:
4535
<A NAME="RM05506SS-7A">7a </A>
Deziel R.
Plante R.
Caron V.
Grenier L.
Llinas-Brunet M.
J. Org. Chem.
1996,
61:
2901
<A NAME="RM05506SS-7B">7b </A>
Captain LF.
Xia X.
Liotta DC.
Tetrahedron Lett.
1996,
37:
4293
<A NAME="RM05506SS-8A">8a </A>
Furukawa J.
Kawabata N.
Nishimura J.
Tetrahedron Lett.
1968,
3495
<A NAME="RM05506SS-8B">8b </A>
Charette AB.
Lemay J.
Angew. Chem., Int. Ed. Engl.
1997,
36:
1090
<A NAME="RM05506SS-9A">9a </A>
Radunz HE.
Eiermann V.
Schneider G.
Riethmueller A.
Tetrahedron
1991,
47:
1887
<A NAME="RM05506SS-9B">9b </A>
Neuman RC.
Rahm ML.
J. Org. Chem.
1966,
31:
1857
<A NAME="RM05506SS-9C">9c </A>
Furrow ME.
Myers AG.
J. Am. Chem. Soc.
2004,
126:
5436
<A NAME="RM05506SS-10">10 </A>
Letsinger RL.
Kammeyer CW.
J. Am. Chem. Soc.
1951,
73:
4476
<A NAME="RM05506SS-11">11 </A>
Jung ME.
Moosman AB.
Lyster MA.
J. Org. Chem.
1978,
43:
3698
<A NAME="RM05506SS-12">12 </A>
Molander GA.
Andrews SW.
Tetrahedron Lett.
1986,
27:
3115
<A NAME="RM05506SS-13">13 </A>
Theberge CR.
Zercher CK.
Tetrahedron
2003,
59:
1521
<A NAME="RM05506SS-14">14 </A>
Charette AB.
Marcoux J.-F.
J. Am. Chem. Soc.
1996,
118:
4539
<A NAME="RM05506SS-15A">15a </A>
Nishimura J.
Kawabata N.
Furukawa J.
Tetrahedron
1969,
25:
2647
<A NAME="RM05506SS-15B">15b </A>
When carbenoid 7 was prepared in the absence of the β-dicarbonyls and allowed to stand for 2 h prior
to quenching by the addition of aqueous acid, 2-iodo-butane was isolated in 54% yield
<A NAME="RM05506SS-16">16 </A>
Blanco L.
Rousseau G.
Barnier JP.
Guibe-Jampel E.
Tetrahedron: Asymmetry
1993,
4:
783
<A NAME="RM05506SS-17">17 </A>
Seyferth D.
Hui Richard C.
Tetrahedron Lett.
1986,
27:
1473
<A NAME="RM05506SS-18">18 </A>
Huang D.
Yan M.
Zhao W.-J.
Shen Q.
Synth. Commun.
2005,
35:
745
<A NAME="RM05506SS-19">19 </A>
Corey EJ.
Hegedus LS.
J. Am. Chem. Soc.
1969,
91:
4926