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Rh-catalyzed π-facial selective intermolecular hydroacylation of norbornenes
Authors:Keitaro Tanaka  Hiroshi Suemune
Institution:Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan
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.
Keywords:Rh-complex  Hydroacylation  Norbornene  π-Facial selection  C-C forming reaction  C-H activation
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