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Base-catalyzed Schmittel cycloisomerization of o-phenylenediyne-linked bis(arenol)s to indeno[1,2-c]chromenes |
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| Authors: | Masaki Furusawa Kosuke Arita Tatsushi Imahori Kazunobu Igawa Katsuhiko Tomooka Ryo Irie |
| Institution: | 1. Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1 Kurokami, Chuo-ku, Kumamoto 860-8555, Japan;2. Priority Organization for Innovation and Excellence, Kumamoto University, 2-39-1 Kurokami, Chuo-ku, Kumamoto 860-8555, Japan;3. Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Japan |
| Abstract: | We describe the transition metal-free base-catalyzed Schmittel cycloisomerization reactions of o-phenylene-linked bis(arenol)s to indeno1,2-c]chromene derivatives through prototropic rearrangement (tautomerization) to a putative vinylidene o-quinone methide intermediate with an enyne-allene system followed by a formal inverse-electron-demand hetero Diels–Alder cycloaddition. The preliminary results on catalytic asymmetric cycloisomerization with chiral bases are also disclosed. |
| Keywords: | Cycloisomerization Domino-reaction Enyne allene Vinylidene o-quinone methide Pseudoazulene |
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