Rh-catalyzed π-facial selective intermolecular hydroacylation of norbornenes |
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Authors: | Keitaro Tanaka Hiroshi Suemune |
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Institution: | Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan |
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Abstract: | Rh-catalyzed π-facial selective intermolecular hydroacylations of norbornenes with salicylaldehyde have been attained. In the reaction with norbornylene, the exo-hydroacylated product was produced because of steric hindrance. In the case of norbornadiene, the endo-product was obtained because of chelation effect. Lastly, because of chelation and remote substituent effects, the product formed in the reaction of 7-tert-butoxynorbornadiene was the endo,syn-product. Deuterium-labeling experiments revealed that the hydroacylation stereoselectively proceeded via endo- and exo-intermediates. |
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Keywords: | Rh-complex Hydroacylation Norbornene π-Facial selection C-C forming reaction C-H activation |
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