Synthesis, Inhaltsverzeichnis Synthesis 2018; 50(09): 1815-1819DOI: 10.1055/s-0036-1591763 psp © Georg Thieme Verlag Stuttgart · New YorkDihydroxylation of Olefins with Potassium Permanganate Catalyzed by Imidazolium Salt Imran Khan School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China eMail: luozb@ujs.edu.cn eMail: xiejm@ujs.edu.cn , Zhi-Bin Luo * School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China eMail: luozb@ujs.edu.cn eMail: xiejm@ujs.edu.cn , Anil Valeru School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China eMail: luozb@ujs.edu.cn eMail: xiejm@ujs.edu.cn , Yin Xu School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China eMail: luozb@ujs.edu.cn eMail: xiejm@ujs.edu.cn , Bin Liu School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China eMail: luozb@ujs.edu.cn eMail: xiejm@ujs.edu.cn , Bhavanarushi Sangepu School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China eMail: luozb@ujs.edu.cn eMail: xiejm@ujs.edu.cn , Ji-Min Xie* School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China eMail: luozb@ujs.edu.cn eMail: xiejm@ujs.edu.cn› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract The development of an efficient and cost-effective cis-dihydroxylation reaction of acrylate derivatives was achieved. The reaction proceeded in acetone with an imidazolium salt as catalyst to furnish the dihydroxylation of olefins at 0–5 °C using KMnO4 as the oxidant. This efficient and non-aqueous protocol was highly suitable for the large-scale preparation of cis-dihydroxylated compounds from the corresponding acrylate derivatives in high yields without overoxidation. Key words Key wordsdihydroxylation - diols - acrylates - potassium permanganate - imidazolium salt Volltext Referenzen References 1a Bolm C. Hildebrand JP. Muñiz K. In Catalytic Asymmetric Synthesis . 2nd ed.; Ojima I. Wiley-VCH; New York: 2000: 399 1b Kolb HC. Van Nieuwenhze MS. Sharpless KB. Chem. Rev. 1994; 94: 2483 1c Schröder M. Chem. Rev. 1980; 80: 187 2a Johnson RA. Sharpless KB. Catalytic Asymmetric Synthesis . 2nd ed.; Ojima I. Wiley-VCH; New York: 2000: 357 2b Gao Y. Cheun Y. Osmium Tetroxide–N-Methylmorpholine N-Oxide. In e-EROS Encyclopedia of Reagents for Organic Synthesis. Wiley; Hoboken: 2013. ; DOI: 10.1002/047084289X.ro009.pub2 2c Chughtai MJ. Donohoe TJ. Gao Y. Harris RM. Kim S.-M. Oh JS. Song C.-E. Yang JW. Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents . Fuchs PL. Wiley; Chichester: 2013. 433 3a Chen K. Que LJr. Angew. Chem. Int. Ed. 1999; 38: 2227 3b Chen K. Costas M. Kim J. Tipton AK. Que LJr. J. Am. Chem. Soc. 2002; 124: 3026 3c Chen K. Costas M. Que LJr. J. Chem. Soc., Dalton Trans. 2002; 672 3d Fujita M. Costas M. Que LJr. J. Am. Chem. Soc. 2003; 125: 9912 3e Klopstra M. Roelfes G. Hage R. Kellogg RM. Feringa BL. Eur. J. Inorg. Chem. 2004; 846 3f Rotthaus O. Le Roy S. Tomas A. Barkigia KM. Artaud I. Inorg. Chim. Acta 2004; 357: 2211 3g De Vos DE. de Wildeman S. Sels BF. Grobet PJ. Jacobs PA. Angew. Chem. Int. Ed. 1999; 38: 980 3h de Boer JW. Brinksma J. Browne WR. Meetsma A. Alsters PL. Hage R. Feringa BL. J. Am. Chem. Soc. 2005; 127: 7990 3i Codola Z. Lloret-Fillol J. Costas M. Prog. Inorg. Chem. 2014; 59: 447 3j Oloo WN. Que LJr. Acc. Chem. Res. 2015; 48: 2612 4 Mergott DJ. Name Reactions for Functional Group Transformations . Li JJ. Corey EJ. Wiley-Interscience; Hoboken: 2007: 327 5a Stewart R. Oxidation Mechanisms: Applications to Organic Chemistry . Benjamin; New York: 1964: 58 5b Wiberg KB. Saebarth KA. J. Am. Chem. Soc. 1957; 79: 2822 5c Lee DG. Brownridge JR. J. Am. Chem. Soc. 1973; 95: 3033 5d Wiberg KB. Deutsch CJ. J. Am. Chem. Soc. 1973; 95: 3034 5e Fatiadi AJ. Synthesis 1987; 85 5f Zimmer R. Collas M. Czerwonka R. Hain U. Reissig H. Synthesis 2008; 237 6a Foglia TA. Barr PA. Malloy AJ. J. Am. Oil Chem. Soc. 1977; 54: 858 6b Watber WP. Shepherd JP. Tetrahedron Lett. 1972; 13: 4907 6c Taylor JE. Williams D. Edwards K. Otonnaa D. Samanich D. Can. J. Chem. 1984; 62: 11 7a Hazra BG. Pore VS. Chordia MD. Bahule BB. Basu S. J. Chem. Res. 2001; 500 7b Hazra BG. Pore VS. J. Indian Chem. Soc. 2003; 80: 1065 8 Bhunnoo RA. Hu Y. Laine DI. Brown RC. D. Angew. Chem. Int. Ed. 2002; 41: 3479 9 Wang C. Zong L. Tan C.-H. J. Am. Chem. Soc. 2015; 137: 10677 10 Luo ZB. Zhao C. Xie JM. Lu HF. Synthesis 2016; 48: 3696 11 Wang J. Xia Q. Drug Delivery 2014; 21: 328 12 Chow W.-S. Liu Y. Che C.-M. Chem. Commun. 2011; 47: 11204 13 Gupta SK. US 20060110415, 2006 14 Borrell M. Costas M. J. Am. Chem. Soc. 2017; 139: 12821 Zusatzmaterial Zusatzmaterial Supporting Information
