Stereoselective Synthesis of Exocyclic Allylsilanes by Intramolecular Reductive Heck Cyclisation of Propargylsilanes
- 1 November 1994
- journal article
- research article
- Published by Wiley in European Journal of Inorganic Chemistry
- Vol. 127 (11), 2235-2240
- https://doi.org/10.1002/cber.1491271123
Abstract
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.This publication has 39 references indexed in Scilit:
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