Tetrahedron

A new synthesis, including asymmetric synthesis, of spiro [4. n] alkenones from three components: cyclic ketones, chloromethyl p-tolyl sulfoxide, and acetonitrile; and a …

T Satoh, T Kawashima, S Takahashi, K Sakai

文献索引：Satoh, Tsuyoshi; Kawashima, Tadashi; Takahashi, Satoru; Sakai, Ken Tetrahedron, 2003 , vol. 59, # 48 p. 9599 - 9607

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被引用次数: 44

摘要

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 ...