Exploring Acetylene Chemistry: A Transition Metal-Free Route to Dienyl 6,8-Dioxabicyclo[3.2.1]octanes from Ketones and Acetylenes
Тип публикации: Journal Article
Дата публикации: 2018-07-20
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30025454
Organic Chemistry
Краткое описание
Dienyl derivatives of 6,8-dioxabicyclo[3.2.1]octanes, closely related to naturally abundant molecules, have been synthesized from 2-acetyl-3,4-dihydropyrans (readily available from ketones and acetylene in two steps), which further add to aryl(hetaryl)acetylenes in the KOBut/DMSO superbase system (105 °C, 1.5 h) to stereoselectively give the corresponding E-styryl adducts. The latter undergo ring closure (NH4Cl/H2O, acetonitrile, reflux, 8 h) to form the 6,8-dioxabicyclo[3.2.1]octane core decorated with the (1 Z,3 E)-diene substituent.
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Schmidt E. Yu. et al. Exploring Acetylene Chemistry: A Transition Metal-Free Route to Dienyl 6,8-Dioxabicyclo[3.2.1]octanes from Ketones and Acetylenes // Journal of Organic Chemistry. 2018. Vol. 83. No. 17. pp. 10272-10280.
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Schmidt E. Yu., Tatarinova I. V., Semenova N. V., Protsuk N. I., Ushakov I., Trofimov B. A. Exploring Acetylene Chemistry: A Transition Metal-Free Route to Dienyl 6,8-Dioxabicyclo[3.2.1]octanes from Ketones and Acetylenes // Journal of Organic Chemistry. 2018. Vol. 83. No. 17. pp. 10272-10280.
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TY - JOUR
DO - 10.1021/acs.joc.8b01449
UR - https://doi.org/10.1021/acs.joc.8b01449
TI - Exploring Acetylene Chemistry: A Transition Metal-Free Route to Dienyl 6,8-Dioxabicyclo[3.2.1]octanes from Ketones and Acetylenes
T2 - Journal of Organic Chemistry
AU - Schmidt, Elena Yu
AU - Tatarinova, Inna V
AU - Semenova, N. V.
AU - Protsuk, Nadezhda I
AU - Ushakov, Igor
AU - Trofimov, B. A.
PY - 2018
DA - 2018/07/20
PB - American Chemical Society (ACS)
SP - 10272-10280
IS - 17
VL - 83
PMID - 30025454
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2018_Schmidt,
author = {Elena Yu Schmidt and Inna V Tatarinova and N. V. Semenova and Nadezhda I Protsuk and Igor Ushakov and B. A. Trofimov},
title = {Exploring Acetylene Chemistry: A Transition Metal-Free Route to Dienyl 6,8-Dioxabicyclo[3.2.1]octanes from Ketones and Acetylenes},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.8b01449},
number = {17},
pages = {10272--10280},
doi = {10.1021/acs.joc.8b01449}
}
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Schmidt, Elena Yu., et al. “Exploring Acetylene Chemistry: A Transition Metal-Free Route to Dienyl 6,8-Dioxabicyclo[3.2.1]octanes from Ketones and Acetylenes.” Journal of Organic Chemistry, vol. 83, no. 17, Jul. 2018, pp. 10272-10280. https://doi.org/10.1021/acs.joc.8b01449.
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