Abstract
The reaction conditions and scope of the photo-Nazarov reaction of aryl vinyl ketones were investigated. In contrast to the conventional acid-catalyzed methods, this photolytic electrocyclization proceeds in the neutral or basic conditions. Irradiating substrates bearing various aromatic rings, acid-sensitive groups, cyclohexenyl, cycloheptenyl, and unsaturated pyran with UV-light (254 nm) smoothly yielded hexahydrofluorenones and related structures. This photo-Nazarov reaction could also be applicable to the substrates carrying β-alkyl groups on the enone, which gave corresponding polycyclic rings containing quaternary centers. These photo-electrocyclized products may prove useful for synthesizing a variety of natural products and their derivatives. Further application of this mild photo-Nazarov reaction in the synthesis of taiwaniaquinol B was achieved.
| Original language | English |
|---|---|
| Pages (from-to) | 8677-8681 |
| Number of pages | 5 |
| Journal | Chemistry - A European Journal |
| Volume | 20 |
| Issue number | 28 |
| DOIs | |
| State | Published - 7 Jul 2014 |
Keywords
- cyclization
- electrocyclic reactions
- ketones
- natural products
- photochemistry
- synthetic methods