| ŠOLOMEK, Tomáš, Peter ŠTACKO, Aneesh TAZHE VEETIL, Tomáš POSPÍŠIL a Petr KLÁN. Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives. Journal of Organic Chemistry. Columbus, OH, USA: the American Chemical Society, 2010, roč. 75, č. 21, s. 7300-7309. ISSN 0022-3263. |
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@article{900530,
author = {Šolomek, Tomáš and Štacko, Peter and Tazhe Veetil, Aneesh and Pospíšil, Tomáš and Klán, Petr},
article_location = {Columbus, OH, USA},
article_number = {21},
keywords = {Photochemistry; Photoenolization},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives},
url = {http://pubs.acs.org/doi/abs/10.1021/jo101515a},
volume = {75},
year = {2010}
}
TY - JOUR
ID - 900530
AU - Šolomek, Tomáš - Štacko, Peter - Tazhe Veetil, Aneesh - Pospíšil, Tomáš - Klán, Petr
PY - 2010
TI - Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives
JF - Journal of Organic Chemistry
VL - 75
IS - 21
SP - 7300-7309
EP - 7300-7309
PB - the American Chemical Society
SN - 00223263
KW - Photochemistry
KW - Photoenolization
UR - http://pubs.acs.org/doi/abs/10.1021/jo101515a
N2 - Irradiation of 2,5-dimethylbenzoyl oxiranes results in a relatively efficient and high-yielding formation of beta-hydroxy functionalized indanones that structurally resemble biologically active pterosines. Nanosecond laser flash photolysis and quantum-chemical calculations based on density functional theory provided evidence that this photochemical transformation proceeds primarily via a photoenolization mechanism. Our study revealed considerable complexity of the mechanism and that structural modifications can significantly alter the reaction pathway and yield different products. The scope of this photochemical transformation for the synthesis of some pharmaceutically important compounds was investigated.
ER -
ŠOLOMEK, Tomáš, Peter ŠTACKO, Aneesh TAZHE VEETIL, Tomáš POSPÍŠIL a Petr KLÁN. Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives. \textit{Journal of Organic Chemistry}. Columbus, OH, USA: the American Chemical Society, 2010, roč.~75, č.~21, s.~7300-7309. ISSN~0022-3263.
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