Synthesis of the Indene, THF, and Pyrrolidine Skeletons by Lewis Acid Mediated Cycloaddition of Methylenecyclopropanes with Aldehydes,N-Tosyl Aldimines, and Acetals
作者:Li-Xiong Shao、Bo Xu、Jin-Wen Huang、Min Shi
DOI:10.1002/chem.200500447
日期:2006.1
Methylenecyclopropanes (MCPs 1) react with aldehydes, N-tosyl aldimines, and acetals to give the corresponding indene, THF, and pyrrolidine cycloaddition products in the presence of BF3 x OEt2 under mild reaction conditions. Some special transformations of MCPs 1 with aldehydes have been reported in this paper. A plausible reaction mechanism has been discussed, which is based on a deuterium-labeling
亚甲基环丙烷(MCP 1)在温和的反应条件下,在BF3 x OEt2存在的情况下,与醛,N-甲苯磺酰胺和缩醛反应,生成相应的茚,THF和吡咯烷环加成产物。本文报道了醛类化合物MCPs 1的一些特殊转化。基于氘标记实验和Prins型反应机理,讨论了可能的反应机理。