A few of my favorite rings: Catalysis inspired by macrocycles

May 2, 2014

Vy M. Dong

Lactones and lactams make up a range of structurally complex and functional compounds, from antibiotics to nanomaterials. Inspired by Nature's cyclic architectures, we are developing catalytic methods that feature stereoselective hydroacylation.1 ,2 Hydroacylation, the formal addition of an aldehyde C–H bond across an unsaturated functional group, is an ideal approach to carbonyl functionalities commonly found in bioactive molecules. We aim to advance hydroacylation as a unified strategy for transforming aldehydes into chiral esters, ketones, and amides. In
this context, my lecture will discuss the design, scope, and mechanism for hydroacylation methods using both rhodium and ruthenium catalysis. Our longterm goal is to develop more green, versatile, and efficient strategies for constructing heterocycles, polyketides, and other biologically relevant motif s.

1 . Murphy, S. K. ; Dong V. M. “Enantioselecti ve Ketone
Hydroacylat ion using Noyo r i ' s Transfer Hydrogenation Catal y s t . ” J .
Am. Chem. Soc. 2013, 135, 5553.
2. von Delius , M. ; Le, C . M. ; Dong V. M. “Rhodium-Phosphoramidi te
Catalyzed A lkene Hydroacylat ion: Mechanism and Octaketide
Natural Product Synthes i s . ” J . Am. Chem. Soc. 2012, 134, 15022.