Catalyst Chelation Effects in Organocatalyzed Ring-Opening Polymerization of Lactide

ACS Macro Lett. 2012 Jan 17;1(1):19-22. doi: 10.1021/mz2000048. Epub 2011 Nov 9.

Abstract

(-)-Sparteine is a proven organocatalyst for the ring-opening polymerization (ROP) of l-lactide, which affords polymers of controlled molecular weight and narrow polydispersity. The recent worldwide shortage of (-)-sparteine has necessitated the identification of simple and cost-effective replacement ROP catalysts. A series of commercially available molecules was first identified through molecular modeling and then subsequently investigated for polymerizing l-lactide. The modeling proved very useful at predicting spatial relationships and nitrogen geometries that greatly aided in the rapid identification of various alkyl amines as alternative organocatalysts.