title: Reactivity studies of 3,3-bis(trimethylsilyl)-2-methyl-1-propene in Lewis acid-catalyzed allylation reactions.
abstract: Allylation reagents, which possess geminal bis-trimethylsilyl substitution, are readily prepared from E- or Z-alkenyl bromides. The reactivity of 3,3-bis(trimethylsilyl)-2-methyl-1-propene (1) is described and predominantly provides ene reactions with aldehydes to give alcohol 2 in the presence of BF3.OEt2. Alternatively, Sakurai allylation reactions of 1 are observed by using stronger Lewis acids in methylene chloride to exclusively yield E-trisubstituted alkenylsilanes 3.
authors.affiliation: Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu
authors.forename: David R
authors.initials: DR
authors.lastname: Williams
authors.forename: Angel I
authors.initials: AI
authors.lastname: Morales-Ramos
authors.forename: Catherine M
authors.initials: CM
authors.lastname: Williams
mesh_terms: D000143:Acids / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: C520937:3,3-bis(trimethylsilyl)-2-methyl-1-propene; D000143:Acids; D000498:Allyl Compounds; D014297:Trimethylsilyl Compounds