Beta-iodoallenolates as springboards for annulation reactions.
Beta-iodoallenolates II, generated from alkynones I with tetra-n-butylammonium iodide and a Lewis acid, underwent selective single or double annulation, depending on the Lewis acid promoter. Treatment with TiCl(4) gave cyclohexenyl alcohols III, whereas BF(3) x OEt(2) gave oxadecalins IV. The scope and limitations of the two annulation reactions are described.
Ciesielski
Jennifer
J
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
Canterbury
Daniel P
DP
Frontier
Alison J
AJ
D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013237:Stereoisomerism
D007659:Ketones; D009281:Naphthalenes; D000644:Quaternary Ammonium Compounds; C110055:allenolic acid