We sought an inexpensive, chiral reagent that could efficiently perform an asymmetric reaction without the need for an expensive transition metal catalyst such as the rhodium complex used in the synthesis of L-DOPA. We decided to start our investigations with the reduction of acetophenone to sec-phenethyl alcohol by a combination of (-)-menthol, a readily available chiral alcohol and lithium aluminum hydride (LiAlH4), a common reducing agent. Similar methodologies are known but not well-developed. In the reaction mixture, (-)-menthol reactions with LiAlH4 to make lithium trimenthoxyaluminum hydride, which then reduces acetophenone to sec-phenethyl alcohol. In our experiments, one enantiomer of sec-phenethyl alcohol was obtained in 87% enantiomeric excess (ee). Decreased temperature lowers the selectivity of the reaction The results of these experiments will be presented and the biological testing of some of the synthesiszed molecules will be discussed

Asymmetric reduction by chiral reagents

240th National Meeting (2010)

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