High-Load, ROMP-Generated Oligomeric Bis-acid Chlorides: Design of Soluble and Insoluble Nucleophile Scavengers
Organic Letters2003Vol. 5(23), pp. 4241–4244
Citations Over TimeTop 12% of 2003 papers
Abstract
[reaction: see text] 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 (SiO(2)), leaving benzoylated nucleophiles in excellent yield and purity.
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