Electronic-State Switching Strategy in the Photochemical Synthesis of lndanones from o-Methyl Phenacyl Epoxides
| Authors | |
|---|---|
| Year of publication | 2011 |
| Type | Article in Periodical |
| Magazine / Source | Organic Letters |
| MU Faculty or unit | |
| 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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