Intramolecular ionic Diels-Alder reactions of α-acetylenic acetals

Seung Bo Shim, Yoon Joo Ko, Byeong Wook Yoo, Chang Keun Lim, Jung Hyu Shin

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The intramolecular ionic Diels-Alder reaction of α-acetylenic acetals as a precursor of the propargyl cation has been investigated in the presence of Lewis acids and in protic acids. The reaction of diene-tethered α-acetylenic acetals (1-2) with formic acid yielded the regioselective intramolecular ionic Diels-Alder reaction products, bicyclodienal (9) and bicyclodienone (11) derivatives, in good yields.

Original languageEnglish
Pages (from-to)8154-8156
Number of pages3
JournalJournal of Organic Chemistry
Volume69
Issue number23
DOIs
Publication statusPublished - Nov 12 2004
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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