An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction.
David A. Petrone
1
,
Eric Fillion
1
Publication type: Journal Article
Publication date: 1997-06-01
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
11671769
Organic Chemistry
Abstract
The tandem "pincer" Diels-Alder reaction, consisting of two consecutive [4 + 2] cycloadditions between two dienes and an acetylenic bis-dienophile, has been applied toward the rapid construction of bridged polyoxacyclic ring systems when furan derivatives are used as the diene components. The study has demonstrated the stereoselectivity (exo-exo adduct), the chemoselectivity ("pincer" vs "domino"), as well as the regioselectivity of the reaction. The reaction has been successfully applied to a variety of 2-substituted furans and tethered bis-furans in combination with monoactivated and diactivated dienophiles. The synthesis of unsymmetrical cycloadducts starting from the aza- and oxanorbornadiene-type intermediate has also been realized.
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55
Total citations:
55
Citations from 2025:
1
(1.82%)
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GOST
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Petrone D. A., Fillion E. An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction. // Journal of Organic Chemistry. 1997. Vol. 62. No. 13. pp. 4418-4427.
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Petrone D. A., Fillion E. An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction. // Journal of Organic Chemistry. 1997. Vol. 62. No. 13. pp. 4418-4427.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo9701593
UR - https://doi.org/10.1021/jo9701593
TI - An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction.
T2 - Journal of Organic Chemistry
AU - Petrone, David A.
AU - Fillion, Eric
PY - 1997
DA - 1997/06/01
PB - American Chemical Society (ACS)
SP - 4418-4427
IS - 13
VL - 62
PMID - 11671769
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{1997_Petrone,
author = {David A. Petrone and Eric Fillion},
title = {An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction.},
journal = {Journal of Organic Chemistry},
year = {1997},
volume = {62},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/jo9701593},
number = {13},
pages = {4418--4427},
doi = {10.1021/jo9701593}
}
Cite this
MLA
Copy
Petrone, David A., and Eric Fillion. “An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction..” Journal of Organic Chemistry, vol. 62, no. 13, Jun. 1997, pp. 4418-4427. https://doi.org/10.1021/jo9701593.