T. Satoh, T. Kawashima, Satoru Takahashi
Nov 24, 2003
Citations
0
Influential Citations
35
Citations
Journal
Tetrahedron
Abstract
Abstract 1-Chlorovinyl p -tolyl sulfoxides were synthesized from several kinds of cyclic ketones and chloromethyl p -tolyl sulfoxide in good yields. Treatment of the 1-chlorovinyl p -tolyl sulfoxides with cyanomethyllithium at −78°C to room temperature gave spirocyclic enaminonitriles in high yields. Acidic treatment of the enaminonitriles afforded spiro[4. n ]alkenones in good yields. By using an unsymmetrical cyclic ketone, α-tetralone, and optically active chloromethyl p -tolyl sulfoxide, this procedure afforded enantiomerically pure spiro[4.5]decenone in good yield with excellent asymmetric induction from the sulfoxide chiral center. By using this method a formal total synthesis of a racemic spirocyclic sesquiterpene, acorone, was realized.