A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes
Тип публикации: Journal Article
Дата публикации: 2003-02-06
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
12608785
Organic Chemistry
Краткое описание
A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ring-closure of 1-oxatrienes.
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Shen H. C. et al. A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes // Journal of Organic Chemistry. 2003. Vol. 68. No. 5. pp. 1729-1735.
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Shen H. C., Wang J., Cole K. P., McLaughlin M. J., Morgan C. D., Douglas C., Hsung R. P., Coverdale H. A., Gerasyuto A. I., Hahn J. M., Liu J., Sklenicka H. M., Wei L., Zehnder L. R., Zificsak C. A. A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes // Journal of Organic Chemistry. 2003. Vol. 68. No. 5. pp. 1729-1735.
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TY - JOUR
DO - 10.1021/jo020688t
UR - https://doi.org/10.1021/jo020688t
TI - A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes
T2 - Journal of Organic Chemistry
AU - Shen, Hong C
AU - Wang, Jiashi
AU - Cole, Kevin P.
AU - McLaughlin, Michael J.
AU - Morgan, Christopher D.
AU - Douglas, Christopher
AU - Hsung, Richard P.
AU - Coverdale, Heather A
AU - Gerasyuto, Aleksey I
AU - Hahn, Juliet M.
AU - Liu, Jia
AU - Sklenicka, Heather M
AU - Wei, Lin-Li
AU - Zehnder, Luke R
AU - Zificsak, Craig A.
PY - 2003
DA - 2003/02/06
PB - American Chemical Society (ACS)
SP - 1729-1735
IS - 5
VL - 68
PMID - 12608785
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2003_Shen,
author = {Hong C Shen and Jiashi Wang and Kevin P. Cole and Michael J. McLaughlin and Christopher D. Morgan and Christopher Douglas and Richard P. Hsung and Heather A Coverdale and Aleksey I Gerasyuto and Juliet M. Hahn and Jia Liu and Heather M Sklenicka and Lin-Li Wei and Luke R Zehnder and Craig A. Zificsak},
title = {A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jo020688t},
number = {5},
pages = {1729--1735},
doi = {10.1021/jo020688t}
}
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Shen, Hong C., et al. “A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes.” Journal of Organic Chemistry, vol. 68, no. 5, Feb. 2003, pp. 1729-1735. https://doi.org/10.1021/jo020688t.