scholarly journals Stereoselective reactions. XIX. Asymmetric dihydroxylation of olefins by employing osmium tetroxide-chiral amine complexes.

1990 ◽  
Vol 38 (8) ◽  
pp. 2133-2135 ◽  
Author(s):  
Kiyoshi TOMIOKA ◽  
Yuichi SHINMI ◽  
Kunihiko SHIINA ◽  
Makoto NAKAJIMA ◽  
Kenji KOGA
Keyword(s):  
Osmium Tetroxide ◽  
Chiral Amine ◽  
Amine Complexes ◽  
Asymmetric Dihydroxylation ◽  
Stereoselective Reactions

Asymmetric dihydroxylation of C,C double bonds using catalytic amounts of osmium tetroxide, selenides, and air

2002 ◽  
Vol 74 (1) ◽  
pp. 107-113 ◽  
Author(s):  
Alain Krief ◽  
Catherine Colaux-Castillo
Keyword(s):  
Potassium Carbonate ◽  
Osmium Tetroxide ◽  
Cinchona Alkaloids ◽  
Double Bonds ◽  
Asymmetric Dihydroxylation ◽  
Tert Butanol

Selenides, selenoxides, osmium tetroxide, and potassium osmate dihydrate are in equilibrium in aqueous tert-butanol containing potassium carbonate. We took advantage of this feature to withdraw the equilibrium in each of the two directions to produce allylalcohols from allylselenides and diols from olefins. The latter reaction performed in the presence of catalytic amounts of Cinchona alkaloids and osmium tetroxide allows the enantioselective dihydroxylation of C,C double bonds.

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