Publication details

Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives

Authors

ŠOLOMEK Tomáš ŠTACKO Peter TAZHE VEETIL Aneesh POSPÍŠIL Tomáš KLÁN Petr

Year of publication 2010
Type Article in Periodical
Magazine / Source Journal of Organic Chemistry
MU Faculty or unit

Faculty of Science

Citation
Web http://pubs.acs.org/doi/abs/10.1021/jo101515a
Field Organic chemistry
Keywords Photochemistry; Photoenolization
Description 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.
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