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Synlett 1991; 1991(10): 684-686
DOI: 10.1055/s-1991-34782
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Stereoselective Synthesis of cis- and trans-β, γ-Unsaturated Carboxylic Esters via Reaction of 1-Alkenyldichloroboranes with Ethyl Diazoacetate

Herbert C. Brown* , Ashok M. Salunkhe
  • *H. C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA
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Publication Date:
13 March 2002 (online)

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trans-1-Alkenyldichloroboranes, easily prepared by the reaction of dichloroborane-dimethyl sulfide complex with various 1-alkynes in the presence of boron trichloride, react smoothly with ethyl diazoacetate at -65 °C with the liberation of nitrogen. Treatment of the intermediates with methanol-water produces trans-β, γ-unsaturated carboxylic esters stereoselectively in good yields. Similar treatment of cis-1-alkenyldichloroboranes provides the corresponding cis-β, γ-unsaturated esters.