Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2007(15): 2404-2408
DOI: 10.1055/s-2007-965886
DOI: 10.1055/s-2007-965886
PAPER
© Georg Thieme Verlag Stuttgart · New York
Formation of β-Substituted γ-Keto Esters via Zinc Carbenoid Mediated Chain Extension
Further Information
Received
22 August 2006
Publication Date:
12 January 2007 (online)
Publication History
Publication Date:
12 January 2007 (online)
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
-
1a
Reissig H.-H. Top. Curr. Chem. 1988, 144: 73 -
1b
Bieraugel H.Akkerman JM.Lapierre Armond JC.Pandit UK. Tetrahedron Lett. 1974, 2817 -
1c
Dowd P.Choi S.-C. J. Am. Chem. Soc. 1987, 109: 3493 -
2a
Brogan JB.Zercher CK. J. Org. Chem. 1997, 62: 6444 -
2b
Hilgenkamp R.Zercher CK. Tetrahedron 2001, 57: 8793 -
2c
Verbicky CA.Zercher CK. J. Org. Chem. 2000, 65: 5615 - 3
Lai S.-J.Zercher CK.Jasinski JP.Reid SN.Staples RJ. Org. Lett. 2001, 3: 4169 - 4
Hilgenkamp R.Zercher CK. Org. Lett. 2001, 3: 3037 - 6
Ronsheim MD.Zercher CK. J. Org. Chem. 2003, 68: 4535 -
7a
Deziel R.Plante R.Caron V.Grenier L.Llinas-Brunet M. J. Org. Chem. 1996, 61: 2901 -
7b
Captain LF.Xia X.Liotta DC. Tetrahedron Lett. 1996, 37: 4293 -
8a
Furukawa J.Kawabata N.Nishimura J. Tetrahedron Lett. 1968, 3495 -
8b
Charette AB.Lemay J. Angew. Chem., Int. Ed. Engl. 1997, 36: 1090 -
9a
Radunz HE.Eiermann V.Schneider G.Riethmueller A. Tetrahedron 1991, 47: 1887 -
9b
Neuman RC.Rahm ML. J. Org. Chem. 1966, 31: 1857 -
9c
Furrow ME.Myers AG. J. Am. Chem. Soc. 2004, 126: 5436 - 10
Letsinger RL.Kammeyer CW. J. Am. Chem. Soc. 1951, 73: 4476 - 11
Jung ME.Moosman AB.Lyster MA. J. Org. Chem. 1978, 43: 3698 - 12
Molander GA.Andrews SW. Tetrahedron Lett. 1986, 27: 3115 - 13
Theberge CR.Zercher CK. Tetrahedron 2003, 59: 1521 - 14
Charette AB.Marcoux J.-F. J. Am. Chem. Soc. 1996, 118: 4539 -
15a
Nishimura J.Kawabata N.Furukawa J. Tetrahedron 1969, 25: 2647 -
15b
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
- 16
Blanco L.Rousseau G.Barnier JP.Guibe-Jampel E. Tetrahedron: Asymmetry 1993, 4: 783 - 17
Seyferth D.Hui Richard C. Tetrahedron Lett. 1986, 27: 1473 - 18
Huang D.Yan M.Zhao W.-J.Shen Q. Synth. Commun. 2005, 35: 745 - 19
Corey EJ.Hegedus LS. J. Am. Chem. Soc. 1969, 91: 4926
References
Pu, Q., unpublished results, University of New Hampshire.