Highly Efficient Solid-State Synthesis of α,β-Epoxy Ketones

Fangfang Ma; Xiaolong Li; Tian Lan; Yongxiang Ma; Baohua Chen; Qingbao Song

doi:10.1055/s-2005-869902

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Synthesis 2005(12): 1945-1948
DOI: 10.1055/s-2005-869902

PAPER

Highly Efficient Solid-State Synthesis of α,β-Epoxy Ketones

Fangfang Ma^a, Xiaolong Li^a, Tian Lan^a, Yongxiang Ma^a, Baohua Chen*^a, Qingbao Song^b
^a Department of Chemistry and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
Fax: +83(931)8912582; e-Mail: chbh@lzu.edu.cn;
^b College of Chemical Engineering and Material Science, Zhejiang University of Technology, Hangzhou 310014, P. R. China

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Publication History

Received 9 December 2004
Publication Date:
24 June 2005 (online)

Abstract
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Abstract

A new solid-state Darzens reaction at room temperature in a mild atmosphere (atmospheric pressure) between aldehydes and α-chloroacetylferrocene resulted in ferrocenyl α,β-epoxy ketones. The main advantages of this procedure are convenient operation, shorter reaction time, excellent yields, high stereoselectivity, cleaner reaction, and low cost.

Keywords

Darzens condensation - solvent-free reaction - ferrocenyl α,β-epoxy ketones - clean reaction

References

1a Parker RE. Isaacs NS. Chem. Rev. 1959, 59: 737

Crossref Google Scholar
1b Rao AS. Paknikar SK. Kirtane JG. Tetrahedron Lett. 1983, 39: 2323

Crossref Google Scholar
1c Smith GJ. Synthesis 1984, 629

Crossref Google Scholar
1d Kotsuki H. Kataoka M. Nishizawa H. Tetrahedron Lett. 1993, 34: 4301

Crossref Google Scholar
1e Alcaraz L. Harnett JJ. Mioskowski C. Martel JP. Gall TL. Shin D.-S. Falk JR. Tetrahedron Lett. 1994, 35: 5449

Crossref Google Scholar
For some recent references, see:
2a Davies HML. Demeese J. Tetrahedron Lett. 2001, 42: 6803

Google Scholar
2b Ahn KH. Park SW. Choi S. Kim H.-J. Moon CJ. Tetrahedron Lett. 2001, 42: 2485

Google Scholar
2c Lydo B. To DMC. Tetrahedron Lett. 2001, 42: 1343

Google Scholar
2d Saito T. Akiba D. Sakashi M. Kanazawa S. Tetrahedron Lett. 2001, 42: 57

Google Scholar
2e Wang Z.-X. Miller SM. Anderson OP. Shi Y. J. Org. Chem. 2001, 66: 521

Google Scholar
2f White MC. Doyle AG. Jacobsen EN. J. Am. Chem. Soc. 2001, 123: 7194

Google Scholar
2g Mitchell JM. Finney NS. J. Am. Chem. Soc. 2001, 123: 862

Google Scholar
2h Doyle MP. Hu W. Timmons DJ. Org. Lett. 2001, 3: 933

Google Scholar
3a Schlögl K. Egger H. Monatsh. Chem. 1963, 94: 376

Crossref Google Scholar
3b Egger H. Schlögl K. J. Organomet. Chem. 1964, 2: 398

Crossref Google Scholar
3c Sevenair JP. Lewis DH. Ponder BW. J. Org. Chem. 1972, 37: 4061

Crossref Google Scholar
3d Schwink L. Knochel P. Eberle T. Okuda J. Organometallics 1998, 17: 7

Crossref Google Scholar
4a Darzens G. C. R. Hebd. Seances Acad. Sci. 1904, 139: 1214

Google Scholar
4b Darzens G. Chem. Zentr. 1905, 1: 346

Google Scholar
4c Darzens G. C. R. Hebd. Seances Acad. Sci. 1905, 141: 766

Google Scholar
4d Darzens G. Chem. Zentr. 1906, 1: 22

Google Scholar
4e Darzens G. C. R. Hebd. Seances Acad. Sci. 1906, 142: 214

Google Scholar
4f Darzens G. Chem. Zentr. 1906, 1: 669

Google Scholar
For some examples, see:
5a Arai S. Shirai Y. Ishida T. Tetrahedron 1999, 55: 6375

Crossref Google Scholar
5b Dagli DJ. Wemple J. J. Org. Chem. 1974, 39: 2938

Crossref Google Scholar
5c Palomo C. Oiarbide M. Sharma AK. González-Rego MC. Linden A. Garcíá JM. González A. J. Org. Chem. 2000, 65: 9007

Crossref Google Scholar
6 Xingxin D. ; Dui Jia Ji Ben Jia Quan De Zhi Bei, In Shi Yong Jing Xi You Ji He Cheng Shou Ce Xingxin D. Huaxue Gongye Publication; Beijing, China: 2002. p.83

Google Scholar
7 Schlögl L. Egger M. Monatsh. Chem. 1962, 95: 376

Google Scholar