The paper shows the efficient conditions for the reduction of R-nitro ketones to give the corresponding nitro alcohols. In some cases the diastereoselectivity was very good (>90:10 anti/syn). The presence of the Lewis acid was found to be pivotal in determining the stereo- chemical outcome of these reactions. Strongly chelating TiCl4 led largely to the anti diastereomer with BH3‚SMe2 as reducing agent.
First TiCl4-Mediated Diastereoslective Reduction of alpha-Nitro Ketones to beta-Nitro Alcohols by BH3.SMe2
BALLINI, Roberto;BOSICA, Giovanna;MARCANTONI, Enrico;VITA, PATRIZIA;
2000-01-01
Abstract
The paper shows the efficient conditions for the reduction of R-nitro ketones to give the corresponding nitro alcohols. In some cases the diastereoselectivity was very good (>90:10 anti/syn). The presence of the Lewis acid was found to be pivotal in determining the stereo- chemical outcome of these reactions. Strongly chelating TiCl4 led largely to the anti diastereomer with BH3‚SMe2 as reducing agent.File in questo prodotto:
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