Saturday, November 17, 2007

Convertion of alkene to ketones

1. hydroboration
alcohol on the less hindered carbon.

2.Wacker oxidation.
very gentle condition. internal alkene is still problematic.

3.alkene to epoxide, then hydride opening of the epoxide gives alcohol on the more substituted carbon. If use Cp2TiCl mediated radical reduction,then gives alcohol on the less hindered carbon.

4. Hg(OAc)2/H2O.
a very gentle condition. gives hydromercury, then NaBH4 radical reduction gives the alcohol on the more substituted carbon.

5. make bromohydrin first, then pd will eliminate the bromide and gives the ketone on the more electronphilic carbon.

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