Electronic-State Switching Strategy in the Photochemical Synthesis of lndanones from o-Methyl Phenacyl Epoxides

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Authors

ŠTACKO Peter ŠOLOMEK Tomáš KLÁN Petr

Year of publication 2011
Type Article in Periodical
Magazine / Source Organic Letters
MU Faculty or unit

Faculty of Science

Citation
Web http://pubs.acs.org/doi/abs/10.1021/ol202892r
Doi http://dx.doi.org/10.1021/ol202892r
Field Organic chemistry
Keywords Photochemistry; synthesis; indanorine; quantum-chemical calculations
Description An electronic excited-state switching strategy has been utilized to control the selectivity of a key photochemical step in the total synthesis of indanorine. The excited-state character of 4,5-dimethoxy-2-methylphenacyl epoxide was changed from an unfavorable (3)pi,pi* state to a productive (3)n,pi* state by a temporary structural modification, resulting in a relatively efficient and high-yielding formation of an indanone derivative. The corresponding structural modification was selected on the basis of quantum chemical calculations prior to the synthesis.
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