Stereocontrolled Synthesis of Tetrasubstituted Double Bonds: Application  to the Construction of Highly Functionalized 4-Alkylidenecyclohexanones

Juris Germanas; K. Peter C. Vollhardt

doi:10.1055/s-1990-21143

Synlett 1990; 1990(9): 505-507
DOI: 10.1055/s-1990-21143

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Stereocontrolled Synthesis of Tetrasubstituted Double Bonds: Application to the Construction of Highly Functionalized 4-Alkylidenecyclohexanones

Juris Germanas^* , K. Peter C. Vollhardt

^*Department of Chemistry, University of California at Berkeley, and the Materials and Chemical Sciences Division, Lawrence Berkeley Laboratory, Berkeley, California 94720, USA

Abstract

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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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