Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation

A facile approach to (E)-alpha-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues. (C) 2012 Elsevier Ltd. All rights reserved.