A method to accomplish a 1,4-addition reaction of bulky nucleophiles to enones and subsequent formation of reactive enolates.
[reaction: see text] BF(3)-promoted 1,4-addition of bulky aryl groups to alpha-iodo enones, prepared from the parent enones, afforded beta-aryl-alpha-iodo ketones. Subsequent reaction with EtMgBr furnished the magnesium enolates, which upon reactions with ClP(O)(OEt)(2) and aldehydes gave enol phosphates and aldols, respectively. This method was applied successfully to a synthesis of Delta(1)-trans-tetrahydrocannabinol.
William
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Department of Biomolecular Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan.
Kobayashi
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Y