Regioselective annulation reaction of 2-arylidene-1,3-indandiones towards synthesis of spirocyclopentenes: Understanding the mechanism of γ-attack: Vs. α-attack using DFT studies

Shaik Anwar*, Li Tzu Lin, V. Srinivasadesikan, Veera Babu Gudise, Kwunmin Chen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

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 (Ea) favour the formation of compound 3avia γ-attack compared to that of 4avia α-attack.

Original languageEnglish
Pages (from-to)38648-38653
Number of pages6
JournalRSC Advances
Volume11
Issue number61
DOIs
Publication statusPublished - 2021 Dec 1

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering

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