Synthesis and Diastereoselective Complexation of Enantiopure Sulfinyl Dienes: The Preparation of Sulfinyl Iron(0) Dienes
The Journal of Organic Chemistry1997Vol. 62(18), pp. 6326–6343
Citations Over TimeTop 10% of 1997 papers
Robert S. Paley, Alfonso de Dios, Lara A. Estroff, Jennifer Lafontaine, Carlos Closa, David J. McCulley, M. Belén Rubio, Maria Paz Ventura, Heather L. Weers, Roberto Fernández de la Pradilla, Sonia de Castro, Rocío Dorado, Miguel Morente
Abstract
The preparation of a diverse array of enantiomerically pure 1- and 2-sulfinyl dienes has been achieved via Stille coupling of halovinyl sulfoxides and vinyl stannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation of the corresponding sulfinyl diene iron(0) tricarbonyl complexes was accomplished by utilizing Fe(CO)5/NMO or (bda)Fe(CO)3 as iron(0) tricarbonyl transfer reagents. Installation of the iron(0) tricarbonyl fragment was shown to be highly diastereoselective (10−16:1) for (R)-(1Z)-1-sulfinyl dienes, most likely as a result of allylic 1,3-strain. The synthesis of a 1-sulfinyl-1,3,8,10-tetraene is also described.
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