1.
RSC Adv
; 11(61): 38648-38653, 2021 Nov 29.
Artigo
em Inglês
| MEDLINE
| ID: mdl-35493224
RESUMO
A regioselective [3+2] cyclisation reaction between 2-arylidene-1,3-indanedione and ethyl 2,3-butadienoate catalysed by triphenylphosphine has been demonstrated to synthesize functionalised spirocyclic cyclopentenes. The reaction tolerated various electron-rich and electron-deficient aryl substituted 2-arylidene-1,3-indanediones with high to excellent chemical yields (up to 99%) and moderate to good regioselectivity (up to 5 : 1). DFT studies have also been carried out to understand the regioselective nature of this reaction. The results of Frontier molecular orbital calculations and the activation energy (E a) favour the formation of compound 3avia γ-attack compared to that of 4avia α-attack.