INTRAMOLECULAR ALLYLATION OF CARBONYL COMPOUNDS. A NEW METHOD FOR FIVE AND SIX MEMBERED RING FORMATION
作者:Junzo Nokami、Shoji Wakabayashi、Rokuro Okawara
DOI:10.1246/cl.1984.869
日期:1984.6.5
By using metallic tin and aluminum in an aqueous medium, ketone having allylic-halides functionality can be cyclized to form five and six membered rings.
Polycyclic derivatives incorporating a cyclopropyl group have been efficiently synthesized from propargyl acetates using platinum(II), gold(I) and gold(III) catalysis. These reactions which are also viable for the preparation of medium-sized rings, proceed with a complete diastereocontrol and can also be run in neat conditions.
The anodic oxidation of 1-acetoxy-1,6-heptadiene homologues in acetic acid gave mainly intramolecular cyclization products, cyclohexenyl ketones. The cyclization takes place through the electrophilic attack of the cationic center generated from the enol ester moiety to the double bond.