Regioselective Synthesis of Trichloromethyl‐Substituted Salicylates and Cyclohexenones by One‐Pot Cyclizations of 1,3‐Bis(trimethylsilyloxy)buta‐1,3‐dienes |
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| Authors: | Sebastian Reimann Alina Bunescu Andranik Petrosyan Muhammad Sharif Silke Erfle Constantin Mamat Tariel V. Ghochikyan Ashot S. Saghyan Anke Spannenberg Alexander Villinger Peter Langer |
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| Affiliation: | 1. Institut für Chemie, Universit?t Rostock, Albert‐Einstein‐Stra?e 3a, DE‐18059 Rostock, (fax: +49‐381‐498‐6412;2. Leibniz Institut für Katalyse an der Universit?t Rostock e.V., Albert‐Einstein‐Stra?e 29a, DE‐18059 Rostock;3. Faculty of Chemistry, Yerevan State University, Alex Manoogian 1, 0025 Yerevan, Armenia;4. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, Pakistan;5. Scientific and Production Center ‘Armbiotechnology' of NAS RA, Gyurjyan str. 14, 0056 Yerevan, Armenia |
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| Abstract: | A variety of 6‐(trichloromethyl)salicylates (=2‐hydroxy‐6‐(trichloromethyl)benzoates) were prepared by TiCl4‐mediated cyclization of 1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes with 1,1,1‐trichloro‐4,4‐dimethoxybut‐3‐en‐2‐one. The employment of trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) as Lewis acid resulted in the formation of trichloromethyl‐substituted cyclohexenones. The cyclizations proceeded with good‐to‐very‐good regioselectivities. |
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| Keywords: | Arene formation Cyclization reactions Salicylates Organochlorine compounds Silyl enol ethers |
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