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Synthesis 1993; 1993(5): 530-536
DOI: 10.1055/s-1993-25899
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Preparation of Functionalized Z-Olefins Using 1,1-Dimetalloalkanes

Charles E. Tucker* , Paul Knochel
  • *Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109, USA
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Publication History

Publication Date:
17 September 2002 (online)

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1,1-Dimetalloalkanes obtained by the allylzincation of alkenylmagnesium compounds react smoothly with various functionalized alkylidenemalonates providing functionalized Z-olefins in good yields. If dimenthyl alkylidenemalonates are used, then excellent stereoselectivities are observed (92:8 to 100:0). An application to a short stereospecific synthesis of an insect pheromone [(Z)-7-dodecenyl acetate] is described (> 99.9% Z, 70% overall yield).

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