Moore Joel D, Byrne Robert J, Vedantham Punitha, Flynn Daniel L, Hanson Paul R
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Org Lett. 2003 Nov 13;5(23):4241-4. doi: 10.1021/ol0352759.
[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.
[反应：见正文] 描述了一种利用由反式双环[2.2.1]庚-5-烯-2,3-二羰基二氯的开环易位聚合反应生成的低聚双酰氯（OBAC）清除大量亲核试剂的有效策略。在常见的苯甲酰化反应后，过量存在的胺、醇和硫醇可利用OBAC试剂的高反应活性和高负载量进行清除。清除反应后，这些低聚物可用乙酸乙酯沉淀并过滤（硅胶），得到产率和纯度优异的苯甲酰化亲核试剂。
