A convenient method for the preparation of oxazaborolidine catalyst in situ using (S)-α,α-diphenylpyrrolidinemethanol, tetrabutylammonium borohydride, and methyl iodide for the asymmetric reduction of prochiral ketones

Anwar, Shaik ; Periasamy, Mariappan (2006) A convenient method for the preparation of oxazaborolidine catalyst in situ using (S)-α,α-diphenylpyrrolidinemethanol, tetrabutylammonium borohydride, and methyl iodide for the asymmetric reduction of prochiral ketones Tetrahedron: Asymmetry, 17 (23). 3244-3247 . ISSN 0957-4166

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...

Related URL: http://dx.doi.org/10.1016/j.tetasy.2006.11.032

Abstract

An oxazaborolidine catalyst is readily prepared in situ at 25°C in THF using (S)-α,α-diphenylpyrrolidinemethanol and borane generated from tetrabutylammonium borohydride/CH3I reagent system. The oxazaborolidine/BH3 reagent system prepared in this way is useful for the reduction of prochiral ketones to the corresponding alcohols with up to 99% ee.

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