Abstract

The synthesis and application of a novel class of chiral 1,2-amino alcohols based on (+)- nopinone is investigated. Mixing a catalytic amount of a ligand with a slight excess of diethylzinc causes a preference for one enantiomer of a chiral tertiary alcohol to be formed upon the addition of an aromatic aldehyde. Other 1,2-amino alcohols used as chiral directors in dialkylzinc reactions (and a myriad of other reactions employing amino alcohol chiral directors) are commonly synthesized from chiral starting materials. However, both enantiomers of said starting material are typically required to produce the set of directors leading to both alcohol enantiomers. Although only a single enantiomer of nopinone is available, it can be used to synthesize two sets of 1,2-amino alcohols 1 and 2 to yield antipodal alcohol products upon the addition of diethylzinc to benzaldehyde. The screening results for several different amino groups as well as the extent of substrate scope will also be described.

Publications:

Binder, C. M.; Dixon, D. D.; Almaraz, E. P.; Tius, M.; Singaram, B. "A Simple Procedure for C-C Bond Cleavage of Aromatic and Aliphatic Epoxides with Aqueous Sodium Periodate Under Ambient Conditions" Tetrahedron Letters, 2008, In Press