Abstract
A stereocontrolled route to tetrasubstituted alkenes applicable to the synthesis of two (E Z) isomeric exocyclic alkenes [4-(2-tert-butyldimethylsiloxy-1-methylethylidene)-2-(3-trimethylsilyl-2-propynyl) cyclohexanones] is described. Iodination of the organomagnesium intermediate obtained by reaction of 4-dibutylamino-2-butyn-1-ol with methylmagnesium bromide afforded a single alkenyl iodide. Conversion to the vinyl copper reagent and reaction with 2-trimethylsilylenones gave acyclic tetrasubstituted alkenones, which were converted to the 4-alkylidenecyclohexanones by ring closure.
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