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Synfacts 2006(12): 1299-1299
DOI: 10.1055/s-2006-955620
DOI: 10.1055/s-2006-955620
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
A New Route to Polymer-Supported Allyltin Reagents
J.-M. Chrétien, F. Zammattio*, D. Gauthier, E. Le Grognec, M. Paris, J.-P. Quintard*
Université de Nantes, , France
Further Information
Publication History
Publication Date:
22 November 2006 (online)
Significance
Polymer-supported triorganotin iodide 1 reacted with allyl bromides 2a-d in the presence of zinc powder to give the polymer-supported allyltin reagents 3a-d in 94-100% conversion (eq. 1). Cerium-mediated allylation reaction of aldehydes 4 with 3a and b provided the corresponding homoallylic alcohols 5 in 74-99% yield (eq. 2). Indium-mediated allylation of aldehydes 4 with 3a,c-d afforded the desired 5 in 72-99% yields (eq. 3). Contamination of organotin residue in the isolated products was controlled at trace level (<60.3 ppm).