The concept of compartmentalization allows the biological cell to perform otherwise incompatible chemical transformations simultaneously and in close proximity. Motivated by nature’s design principles we describe an amphiphilic poly(2-oxazoline) tri-block copolymer with three covalently attached catalysts that are spatially separated from one another. This polymeric support structure assembles into spherical micelles with carboxylic acids in the hydrophilic corona, Rh-TsDPEN catalysts in the cross-linked shell, and 4-Dimethylaminopyridine (DMAP) inside the hydrophobic core. The spatial positioning of each catalyst in the shell cross-linked micelle (SCM) is designed to exploit the path of the substrate during each step of the non-orthogonal tandem reaction: Ketal hydrolysis to a prochiral ketone, asymmetric transfer hydrogenation (ATH) to an enantioenriched secondary alcohol, acylation to the final ester product.

Shell cross-linked micelles (SCM)s as nanoreactors for enantioselective three step tandem catalysis

256th National Meeting (2018)

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