p-Menthane-3-carboxaldehyde serves as an efficient chiral auxiliary in the preparation of chiral non-racemic S-alkylthiocarbamates or S-dithiocarbonates via the 3,3-sigmatropic rearrangement of the corresponding alkylthionocarbamates or xanthates. The transfer of chirality during rearrangement is complete, and the final products possess a chiral tertiary or quaternary carbon bearing sulfur. The rearranged products are then transformed into enantiopure cyclic or acyclic sulfur-containing products, depending on the means of clivage of the auxiliary. The synthesis of a potent MMP-13 inhibitor is presented.Key words: 3,3-sigmatropic rearrangement, p-menthane-3-carboxaldehyde, S-alkylthiocarbamate, S-dithiocarbonate, alkylthionocarbamate, xanthate, ring-closing metathesis.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.