Construction of cyclopenta[: B] pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes

Xuefeng Liang, Weijian Ye, Waygen Thor, Lantian Sun, Bo Wang, Shuzhong He, Yuen Kit CHENG, Chi Sing LEE*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A method for synthesising cyclopenta[b]pyran-2-ones through direct (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes is described. In the presence of Pd2(dba)3/dppe in toluene, a series of 2-pyrones undergo chemoselective (3 + 2) cycloaddition with vinyl cyclopropanes and afford cyclopenta[b]pyran-2-ones in high yields (78-96%). The trans/cis ratio of the cycloadducts has been optimised up to 10:1. The proposed mechanism of this cycloaddition has been rationalised by computational studies.

Original languageEnglish
Pages (from-to)840-845
Number of pages6
JournalOrganic Chemistry Frontiers
Volume7
Issue number6
DOIs
Publication statusPublished - 21 Mar 2020

Scopus Subject Areas

  • Organic Chemistry

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