Intramolecular ionic Diels-Alder reactions of α-acetylenic acetals

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

doi:10.1021/jo048867t

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 journal › Article › peer-review

6 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 language	English
Pages (from-to)	8154-8156
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	69
Issue number	23
DOIs	https://doi.org/10.1021/jo048867t
Publication status	Published - Nov 12 2004
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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AU - Shim, Seung Bo

AU - Ko, Yoon Joo

AU - Yoo, Byeong Wook

AU - Lim, Chang Keun

AU - Shin, Jung Hyu

PY - 2004/11/12

Y1 - 2004/11/12

N2 - 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.

AB - 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.

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Intramolecular ionic Diels-Alder reactions of α-acetylenic acetals

Abstract

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