Lewis acid-catalyzed [4 + 3] cycloaddition of 2-(trimethyl silyloxy)acrolein with furan. Insight on the nature of the mechanism from a DFT analysis.
[reaction: see text]. The mechanism for the Lewis acid-catalyzed [4 + 3] cycloaddition of 2-(trimethylsilyloxy)acrolein 1 with furan 2 has been studied at the B3LYP/6-31G level. This reaction is a three-step process that is initialized by the nucleophilic attack of 2 to the beta-conjugated position of 1 to give a zwitterionic intermediate IN1. The key step on the formation of the seven-membered ring is the electrophilic attack of the furan residue to the electrophilically activated carbonyl carbon at this intermediate.
Instituto de Ciencia Molecular, Universidad de Valencia, Dr. Moliner 50, E-46100 Burjassot, Valencia, Spain.
José A
JA
Sáez
Manuel
M
Arnó
Luis R
LR
Domingo