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The stereoselective palladium‐catalysed synthesis of the heterocycles 13‐15 with a (Z)‐exocyclic allylsilane moiety is described. Alkylation of the secondary amides 5a, 5b, 9a, and 9b and the phenol 11 containing an iodoaryl moiety with the propargyl iodide 6 leads to the propargylsilanes 7a, 7b, 10a, 10b, and 12, which are allowed to react with a catalyst system of Pd(OAc)2/PPh3/NPr4Br and sodium formate as a hydride source. The (Z) configuration of the cyclisation products is confirmed by NOESY spectra and a single‐crystal X‐ray structure of 13b.
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Tietze et al. (1994) studied this question.
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