Tetrahedron

Sequential alkynylation of ω-bromoalkyl triflates: facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones

RJ Armstrong-Chong, K Matthews, JM Chong

Index: Armstrong-Chong, Rosemary J.; Matthews, Kristopher; Chong, J. Michael Tetrahedron, 2004 , vol. 60, # 45 p. 10239 - 10244

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Citation Number: 12

Abstract

Sequential treatment of ω-bromoalkyl triflates with an alkynyllithium at 0° C followed by addition of a second alkynyllithium and NaI and heating the reaction mixture provides a simple one-pot access to unsymmetrical diynes in good yields. These diynes may be transformed stereoselectively into diene pheromones such as (Z, Z)-and (E, Z)-3, 13- octadecadienyl acetate.