Carbocyclization reaction of active methine compounds with unactivated alkenyl or alkynyl groups mediated by TiCl4-Et3N

Osamu Kitagawa, Takashi Suzuki, Tadashi Inoue, Yoko Watanabe, Takeo Taguchi

研究成果: Article査読

72 被引用数 (Scopus)

抄録

In the presence of TiCl4, Et3N, and I2, iodocarbocyclization reaction of various active methine compounds having alkenyl groups gave iodocycloalkane derivatives in good yields. On the other hand, TiCl4 and Et3N promote the carbocyclization of active methine compounds with 4- alkynyl groups in the absence of I2 to give methylenecyclopentane derivatives in good yields. This reaction proceeds with high streoselectivity through a cis-addition of trichlorotitanium enolates of active methine compounds to alkynes, and the resulting vinyltitanium intermediates can be further functionalized by the reaction with various electrophiles.

本文言語English
ページ(範囲)9470-9475
ページ数6
ジャーナルJournal of Organic Chemistry
63
25
DOI
出版ステータスPublished - 1998 12 11
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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