title: Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes.
abstract: The synthesis of densly functionized α-silyl-β-hydroxyl vinylsilanes via ruthenium-catalyzed multicomponent reaction (MCR) is reported herein. Exceptionally high regio- and diastereoselectivity was achieved by employing an unprecedented hydrosilylation of bifunctional silyl-propargyl boronates. The simple protocol, mild reaction conditions, and unique tolerability of this method make it a valuable tool for the synthesis of highly elaborated building blocks. The one-pot synthesis of stereodefined olefins, the generation of a valuable cyclohexene building block through a four-component MCR, and further functionalization in an abundance of diastereoselective reactions is disclosed herein.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California, 94305-5080, USA. bmtrost@stanford.edu.
authors.forename: Barry M
authors.identifier: http://orcid.org/0000-0001-7369-9121
authors.initials: BM
authors.lastname: Trost
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California, 94305-5080, USA.
authors.forename: Dennis C
authors.initials: DC
authors.lastname: Koester
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California, 94305-5080, USA.
authors.forename: Ehesan U
authors.initials: EU
authors.lastname: Sharif
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D053138:Cyclohexenes; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D053138:Cyclohexenes; D012821:Silanes; D014753:Vinyl Compounds; C476909:vinylsilane; D012428:Ruthenium
keywords: catalysis; dienes; ruthenium; silanes; stereoselectivity