Oxidation of saturated and unsaturated alcohols promoted by aluminum alkyls and t-butyl hydroperoxide

作者: Antonio Proto , Carmine Capacchione , Arrigo Scettri , Oriana Motta

DOI: 10.1016/S0926-860X(03)00081-4

关键词:

摘要: Saturated and unsaturated alcohols are efficiently converted into the corresponding ketones epoxy-alcohols by treatment with organic aluminium compounds/t-butyl hydroperoxide systems. In this paper, we have exploited possibility of using some commercial alkyls as catalysts for oxidation reactions. Then, since observed that increase hindrance on enhances conversion toward oxidated products, found interest to synthesize a more hindered based compound. The catalytic performance latter compound reactions allylic was tested it is most attractive both in terms yield time reaction.

参考文章(11)
Laura Palombi, Arrigo Scettri, Alessandra Barrella, Antonio Proto, Epoxidation and oxidation of alcohols. A new procedure using the methylalumoxane/tert-butyl hydroperoxide system Green Chemistry. ,vol. 1, pp. 27- 29 ,(1999) , 10.1039/A809768B
Laura Palombi, Francesco Bonadies, Arrigo Scettri, MICROWAVE-ASSISTED OXIDATION OF SATURATED AND UNSATURATED : ALCOHOLS WITH T-BUTYL HYDROPEROXIDE AND ZEOLITES Tetrahedron. ,vol. 53, pp. 15867- 15876 ,(1997) , 10.1016/S0040-4020(97)10047-3
Laura Palombi, Francesco Bonadies, Arrigo Scettri, Diastereoselective epoxidation of allylic alcohols by t-butyl hydroperoxide/zeolites system Tetrahedron. ,vol. 53, pp. 11369- 11376 ,(1997) , 10.1016/S0040-4020(97)00718-7
Leo A. Paquette, Robert J. Ross, James P. Springer, Stereocontrolled construction of an ingenol prototype having a complete array of oxygenated and unsaturated centers. Journal of the American Chemical Society. ,vol. 110, pp. 6192- 6204 ,(1988) , 10.1021/JA00226A039
Kazuhiko Takai, Koichiro Oshima, Hitosi Nozaki, Selective oxidation with t-butyl hydroperoxide and aluminium reagents Tetrahedron Letters. ,vol. 21, pp. 1657- 1660 ,(1980) , 10.1016/S0040-4039(00)77778-1
Y. Kishi, Total synthesis of rifamycin S Pure and Applied Chemistry. ,vol. 53, pp. 1163- 1180 ,(1981) , 10.1351/PAC198153061163
R.J.P. Corriu, C. Guerin, Nucleophilic substitution at silicon: Evidence for electronic factors as driving force of the stereochemistry Journal of Organometallic Chemistry. ,vol. 144, pp. 165- 173 ,(1978) , 10.1016/S0022-328X(00)84159-5
Tetsuo Tsuda, Toshio Hayashi, Hiroshi Satomi, Tadashi Kawamoto, Takeo Saegusa, Methylcopper(I)-catalyzed selective conjugate reduction of α,β-unsaturated carbonyl compounds by diisobutylaluminum hydride in the presence of hexamethylphosphoric triamide Journal of Organic Chemistry. ,vol. 51, pp. 537- 540 ,(1986) , 10.1021/JO00354A027
Laura Palombi, Francesco Bonadies, Arrigo Scettri, Aluminosilicate-catalyzed oxidation of alcohols by t-butyl hydroperoxide Journal of Molecular Catalysis A-chemical. ,vol. 140, pp. 47- 53 ,(1999) , 10.1016/S1381-1169(98)00217-9
H. Nagaoka, W. Rutsch, G. Schmid, H. Iio, M. R. Johnson, Y. Kishi, Total synthesis of rifamycins. 1. Stereocontrolled synthesis of the aliphatic building block Journal of the American Chemical Society. ,vol. 102, pp. 7962- 7965 ,(1980) , 10.1021/JA00547A037