Abstract
The enantioselective allylation of aldehydes are considered one of the most useful carbon-carbon bond forming reactions in synthetic chemistry. This reaction type is of such use because it allows access to a wide range of homoallylic alcohols, which are considered a common building block for a number of biologically active natural products. Although there are a number of asymmetric allylation strategies reported currently, most processes involve: reagents or catalysts sensitive to air and moisture, catalysts incorporating toxic metals, toxic allylstannanes, and/or stochiometric amounts of chiral initiators. The use of chiral imidazolidinones as catalysts to perform directed additions of allyl indiums to aldehydes was investigated. This approach would eliminate many of the disadvantageous means or materials used in other methodologies while providing the same chiral alcohols. A range of aldehydes and allyl halides were studied using this methodology. Products were recovered in high yield (64-93%). One reaction proved asymmetric with an enantiomeric excess (ee) of >99%. Changes to solvent, catalyst, and co-catalyst were investigated illuminating key insights into the way in which this reaction proceeds. Results of these assorted studies revealed information about catalyst function and the rate of reactions possible in this one-pot mixture.