title: The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.
abstract: In investigations aimed at exploring the potential of disubstituted allenes in stereoselective synthesis, we report studies that explore the reductive cross-coupling reaction of vinylsilanes with a range of substituted allenes. Regiochemical control is attained by employing allenic alkoxides, where the proximal heteroatom dictates the site-selectivity in a process that proceeds by net formal metallo-[3,3] rearrangement (directed carbometalation/elimination). Stereoselectivity in these reactions is complex, with both the nature of allene substitution and relative stereochemistry of the substrate impacting the stereoselective generation of each alkene of a substituted 1,3-diene. 2009 Elsevier Ltd. All rights reserved.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, FL 33458.
authors.forename: Allan U
authors.initials: AU
authors.lastname: Barlan
authors.forename: Glenn C
authors.initials: GC
authors.lastname: Micalizio
keywords: Allenes; Reductive Cross-Coupling; Titanium; Z-dienes
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