title: Synthesis of spirocarbamate oxindoles via intramolecular trapping of a β-silyl carbocation by an N-Boc group.
abstract: We report the Lewis acid catalyzed additions of allylsilanes to N-Boc-iminooxindoles and the formation of novel silicon-containing spirocarbamates via intramolecular trapping of a β-silyl carbocation by an N-Boc group. Several transformations display the synthetic utility of these spirocarbamate oxindoles, including a reductive cyclization to access new silylated furoindoline derivatives.
authors.affiliation: Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA.
authors.forename: Benjamin H
authors.initials: BH
authors.lastname: Shupe
authors.forename: Emily E
authors.initials: EE
authors.lastname: Allen
authors.forename: Jacob P
authors.initials: JP
authors.lastname: MacDonald
authors.forename: Sean O
authors.initials: SO
authors.lastname: Wilson
authors.forename: Annaliese K
authors.initials: AK
authors.lastname: Franz
mesh_terms: D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002412:Cations / Q000737:chemistry*; D005563:Formic Acid Esters / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D012821:Silanes / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002219:Carbamates; D002412:Cations; D005563:Formic Acid Esters; D007211:Indoles; D000078183:Oxindoles; D012821:Silanes; D013141:Spiro Compounds; C000345:t-butyloxycarbonyl group; C022960:2-oxindole