Reactivity studies of 3,3-bis(trimethylsilyl)-2-methyl-1-propene in Lewis acid-catalyzed allylation reactions.
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.
Williams
David R
DR
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu
Morales-Ramos
Angel I
AI
Williams
Catherine M
CM
D000143:Acids / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
C520937:3,3-bis(trimethylsilyl)-2-methyl-1-propene; D000143:Acids; D000498:Allyl Compounds; D014297:Trimethylsilyl Compounds