Versatile Precursors for the Synthesis of Enynes and Enediynes
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Alauddin, Mian M.
Fuhry, Marry Ann M.
Dragovich, Peter S.
Finney, Nathaniel S.
Harrington, Philip M.
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CitationMyers, Andrew G., Mian M. Alauddin, Mary Ann M. Fuhry, Peter S. Dragovich, Nathaniel S. Finney, and Philip M. Harrington. 1989. Versatile precursors for the synthesis of enynes and enediynes. Tetrahedron Letters 30(50): 6997-7000.
Abstract(Z)-Ethyl 2,3-dibromoproenoate, readily available in multigram quantities, undergoes selective replacement of the B-bromide in coupling reactions with trimethyl-silylacetylene to produce the (Z)-enyne 2. This product may be further elaborated to various functionalized enynes of defined geometry or may be coupled with a second acetylenic reactant to produce (Z)-enediynes.
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