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

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 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

Access to Document

10.1021/jo048867t

Fingerprint Dive into the research topics of 'Intramolecular ionic Diels-Alder reactions of α-acetylenic acetals'. Together they form a unique fingerprint.

Cite this

@article{2c2e81a2323f4a96aa68686382593bf2,

title = "Intramolecular ionic Diels-Alder reactions of α-acetylenic acetals",

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.",

author = "Shim, {Seung Bo} and Ko, {Yoon Joo} and Yoo, {Byeong Wook} and Lim, {Chang Keun} and Shin, {Jung Hyu}",

year = "2004",

month = nov,

day = "12",

doi = "10.1021/jo048867t",

language = "English",

volume = "69",

pages = "8154--8156",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Intramolecular ionic Diels-Alder reactions of α-acetylenic acetals

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.

UR - http://www.scopus.com/inward/record.url?scp=8644229233&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=8644229233&partnerID=8YFLogxK

U2 - 10.1021/jo048867t

DO - 10.1021/jo048867t

M3 - Article

AN - SCOPUS:8644229233

VL - 69

SP - 8154

EP - 8156

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -