Iodocarbocyclization reaction

Osamu Kitagawa, Tadashi Inoue, Takeo Taguchi

研究成果: Article査読

20 被引用数 (Scopus)

抄録

The "halocarbocyclization reaction", which involves an intramolecular attack of a carbon nucleophile on a double bond activated by an electrophilic halogenating reagent, has so far been uncommon. We report here that the "iodocarbocyclization reaction" of alkenyl or alkynylmalonate derivatives proceeded in good yields in the presence of Ti(OR)4 and I2 to give cyclized products in a highly regio- and stereospecific manner. The diastereoselective iodocarbocyclization with 4-pentenylmalonate derivatives having a chiral center at the allylic or homoallylic position and allylmalonate having a chiral auxiliary in the ester part has also been investigated. Furthermore, the reaction of 4-pentenylmalonate using a catalytic amount of a chiral titanium alkoxide in the presence of I2 and 2,6-dimethoxypyridine proceeded with high enantioselectivity to give good yields of cyclopentane derivatives. The origin of enantioselectivity in this catalytic asymmetric reaction is also described.

本文言語English
ページ(範囲)243-262
ページ数20
ジャーナルReviews on Heteroatom Chemistry
15
出版ステータスPublished - 1997 12 1
外部発表はい

ASJC Scopus subject areas

  • 無機化学

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