Enantioselective protonation is a common process in biosynthetic sequences. The decarboxylase and esterase enzymes that effect this valuable transformation are able to control both the steric environment around the proton acceptor (typically an enolate) and the proton donor (typically a thiol). Recently, several chemical methods for achieving enantioselective protonation have been developed by exploiting various means of enantiocontrol in different mechanisms. These laboratory transformations have proved useful for the preparation of a number of valuable organic compounds. Here, we review recent reports of enantioselective protonations, classifying them according to mechanism, and discuss how a deeper understanding of the processes can lead to improved methods for effecting this most fundamental method of obtaining enantiopure compounds.
Additional Information© 2009 Nature Publishing Group. Published online: 24 July 2009. We thank the National Institutes of Health, National Institute of General Medical Sciences (grant number R01GM080269-01), Eli Lilly (predoctoral fellowship to J.T.M.), Amgen, Abbott Laboratories, Boehringer Ingelheim, Merck, Bristol-Myers Squibb and the California Institute of Technology for financial support.
Accepted Version - nihms194130.pdf