PREVOST WOODWARD Olefin

A recent example L. Emmanuvel, T.M. A. Shaikh, A. Sudalai, Nal04 / LiBr-mediated diastereoselective dihydroxylation of olefins a catalytic approach to the Prevost-Woodward reaction, Org. Lett. 7 (2005) 5071-5074. 

Vicinal iodo carboxylates may also be prepared from the reaction of olefins either with iodine and potassium iodate in acetic acid/ or with N-iodosuccinimide and a carboxylic acid in chloroform. " A number of new procedures for effecting the hydroxylation or acyloxylation of olefins in a manner similar to the Prevost or Woodward-Prevost reactions include the following iodo acetoxylation with iodine and potassium chlorate in acetic acid followed by acetolysis with potassium acetate reaction with iV-bromoacetamide and silver acetate in acetic acid reaction with thallium(III) acetate in acetic acid and reaction with iodine tris(trifluoroacetate) in pentane. ... 

Despite the dominance of dihydroxylation reactions employing Os(VlIl) for the production of vicinal diols, alternatives have been utilized in asymmetric syntheses. The best known of these is perhaps Woodward s modification [205] of the Prevost reaction [206]. This classic oxidation is known to generally yield anti-1,2-diacetates from olefinic substrates [207]. Woodward s key modification involves the inclusion of water in the reaction mixture. The intermediate iodo-acetate 303 undergoes hydrolytic cleavage... 

---