Chiral diols offer a potentially simple way to resolve racemic mixtures of aldehydes and ketones through the formation of acetals. The resulting diastereomeric acetals may be separated by normal means. After separation has been achieved, a simple deprotection in aqueous acid will yield the resolved aldehyde (or ketone) and the chiral diol which can be recycled for future use. This project produced a chiral diol from the TADDOL family of compounds, and the chirality centers in the diol product originate from the starting material for the reaction sequence: L-tartaric acid. Initial studies are underway to probe the utility of chiral diols in the separation of racemic mixtures.

Diols as chiral auxiliaries in the separation of racemic mixtures

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.