Synthesis of the indene, THF, and pyrrolidine skeletons by Lewis acid mediated cycloaddition of methylenecyclopropanes with aldehydes, N-tosyl aldimines, and acetals.
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 experiment and the Prins-type reaction mechanism.
Shao
Li-Xiong
LX
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Xu
Bo
B
Huang
Jin-Wen
JW
Shi
Min
M