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Asymmetric Reduction of Ketones

By: William Sommer , Aldrich ChemFiles 2008, 8.6, 5.

Aldrich ChemFiles 2008, 8.6, 5.

The enantioselective reduction of ketones to alcohols gives access to a pool of chiral building blocks that can be used for the synthesis of natural products. Adolfsson and co-workers reported a novel class of ligands, based on a pseudo-dipeptide,1 for the mild and efficient reduction of ketones using 2-propanol as a hydrogen source. The ligand is used with [{RuCl2(p-cymene)}2] in presence of NaOH for the asymmetric reduction of a variety of acetophenone derivatives. Excellent yields and ee’s were reported (Scheme 1).

Scheme 1.

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  1. Bøgevig, A. et al. Chem. Eur. J. 2004, 10, 294.; Västilä, P. et al. Chem. Commun. 2005, 4039.

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