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

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

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

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Referenzen

References

<A NAME="RF18204SS-1A">1a</A> Parker RE. Isaacs NS. Chem. Rev. 1959, 59: 737

<A NAME="RF18204SS-1B">1b</A> Rao AS. Paknikar SK. Kirtane JG. Tetrahedron Lett. 1983, 39: 2323

<A NAME="RF18204SS-1C">1c</A> Smith GJ. Synthesis 1984, 629

<A NAME="RF18204SS-1D">1d</A> Kotsuki H. Kataoka M. Nishizawa H. Tetrahedron Lett. 1993, 34: 4301

<A NAME="RF18204SS-1E">1e</A> Alcaraz L. Harnett JJ. Mioskowski C. Martel JP. Gall TL. Shin D.-S. Falk JR. Tetrahedron Lett. 1994, 35: 5449

For some recent references, see:

<A NAME="RF18204SS-2A">2a</A> Davies HML. Demeese J. Tetrahedron Lett. 2001, 42: 6803

<A NAME="RF18204SS-2B">2b</A> Ahn KH. Park SW. Choi S. Kim H.-J. Moon CJ. Tetrahedron Lett. 2001, 42: 2485

<A NAME="RF18204SS-2C">2c</A> Lydo B. To DMC. Tetrahedron Lett. 2001, 42: 1343

<A NAME="RF18204SS-2D">2d</A> Saito T. Akiba D. Sakashi M. Kanazawa S. Tetrahedron Lett. 2001, 42: 57

<A NAME="RF18204SS-2E">2e</A> Wang Z.-X. Miller SM. Anderson OP. Shi Y. J. Org. Chem. 2001, 66: 521

<A NAME="RF18204SS-2F">2f</A> White MC. Doyle AG. Jacobsen EN. J. Am. Chem. Soc. 2001, 123: 7194

<A NAME="RF18204SS-2G">2g</A> Mitchell JM. Finney NS. J. Am. Chem. Soc. 2001, 123: 862

<A NAME="RF18204SS-2H">2h</A> Doyle MP. Hu W. Timmons DJ. Org. Lett. 2001, 3: 933

<A NAME="RF18204SS-3A">3a</A> Schlögl K. Egger H. Monatsh. Chem. 1963, 94: 376

<A NAME="RF18204SS-3B">3b</A> Egger H. Schlögl K. J. Organomet. Chem. 1964, 2: 398

<A NAME="RF18204SS-3C">3c</A> Sevenair JP. Lewis DH. Ponder BW. J. Org. Chem. 1972, 37: 4061

<A NAME="RF18204SS-3D">3d</A> Schwink L. Knochel P. Eberle T. Okuda J. Organometallics 1998, 17: 7

<A NAME="RF18204SS-4A">4a</A> Darzens G. C. R. Hebd. Seances Acad. Sci. 1904, 139: 1214

<A NAME="RF18204SS-4B">4b</A> Darzens G. Chem. Zentr. 1905, 1: 346

<A NAME="RF18204SS-4C">4c</A> Darzens G. C. R. Hebd. Seances Acad. Sci. 1905, 141: 766

<A NAME="RF18204SS-4D">4d</A> Darzens G. Chem. Zentr. 1906, 1: 22

<A NAME="RF18204SS-4E">4e</A> Darzens G. C. R. Hebd. Seances Acad. Sci. 1906, 142: 214

<A NAME="RF18204SS-4F">4f</A> Darzens G. Chem. Zentr. 1906, 1: 669

For some examples, see:

<A NAME="RF18204SS-5A">5a</A> Arai S. Shirai Y. Ishida T. Tetrahedron 1999, 55: 6375

<A NAME="RF18204SS-5B">5b</A> Dagli DJ. Wemple J. J. Org. Chem. 1974, 39: 2938

<A NAME="RF18204SS-5C">5c</A> Palomo C. Oiarbide M. Sharma AK. González-Rego MC. Linden A. Garcíá JM. González A. J. Org. Chem. 2000, 65: 9007

<A NAME="RF18204SS-6">6</A> 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

<A NAME="RF18204SS-7">7</A> Schlögl L. Egger M. Monatsh. Chem. 1962, 95: 376