High-Load, ROMP-Generated Oligomeric Bis-acid Chlorides:  Design of Soluble and Insoluble Nucleophile Scavengers

Autor: Moore, J. D., Byrne, R. J., Vedantham, P., Flynn, D. L., Hanson, P. R.
Zdroj: Organic Letters; November 2003, Vol. 5 Issue: 23 p4241-4244, 4p
Abstrakt: An efficient strategy for scavenging a host of nucleophiles utilizing an oligomeric bis-acid chloride (OBAC), generated from the ROM polymerization of trans-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyl dichloride, is described. The reactivity and high load of the OBAC reagent is exploited in the scavenging of amines, alcohols, and thiols that are present in excess following a common benzoylation event. Following the scavenging event, these oligomers can be precipitated with EtOAc and filtered (SiO2), leaving benzoylated nucleophiles in excellent yield and purity.
Databáze: Supplemental Index