An improved catalytic OsO4 oxidation of olefins to -1,2-glycols using tertiary amine oxides as the oxidant

Tetrahedron Letters - Tập 17 Số 23 - Trang 1973-1976 - 1976
V. VanRheenen1, Robert C. Kelly1, D.Y. Cha1
1The Upjohn Company Kalamazoo, Michigan 49001 U.S.A.

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Tài liệu tham khảo

Gundstone, 1960, 1, 110ff

Hofmann, 1912, Ber., 45, 3329, 10.1002/cber.19120450381

Milas, 1936, J. Am. Chem. Soc., 58, 1302, 10.1021/ja01298a065

Milas, 1959, J. Am. Chem. Soc., 81, 4730, 10.1021/ja01526a070

Norton, 1965, Selective Oxidation Processes, Advances in Chemistry Series, No. 51, Amer. Chem. Soc., 10

Kelly, 1973, Advances in Chemistry Series, No. 51, Amer. Chem. Soc., 95, 2746, 10.1021/ja00789a089

W. P. Schneider, A. R. Hanze, U.S. Patent 2,769,823.

Clark, 1949, J. Chem. Soc., 315, 10.1039/jr9490000315

Lloyd, 1972, Synthesis, 610, 10.1055/s-1972-21948

Cope, 1952, J. Am. Chem. Soc., 74, 5884, 10.1021/ja01143a018

Weber, 1972, Tetra. Lett., 4907, 10.1016/S0040-4039(01)94462-4

Tanaka, 1972, J. Biol. Chem., 247, 7465, 10.1016/S0021-9258(19)44549-3

Jernow, 1971, J. Org. Chem., 36, 3511, 10.1021/jo00822a009

Shealy, 1969, J. Am. Chem. Soc., 91, 3075, 10.1021/ja01039a042

W. P. Schneider, A. V. McIntosh, U.S. Patent 2,769,824. The use of NMO in catalytic OsO4 reactions was first disclosed in this patent during work to introduce the cortico side chain (an α-ketol) in a steroid.

Magerlein, 1975, Prostaglandins, 9, 5, 10.1016/S0090-6980(75)80112-2

Kelly, 1973, J. Am. Chem. Soc., 95, 7156, 10.1021/ja00802a043

Sharpless, 1976, J. Am. Chem. Soc., 98, 1986, 10.1021/ja00423a067