Iodocarbocyclization reaction

Osamu Kitagawa, Tadashi Inoue, Takeo Taguchi

研究成果: Article

20 引用 (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.

元の言語English
ページ(範囲)243-262
ページ数20
ジャーナルReviews on Heteroatom Chemistry
15
出版物ステータスPublished - 1996
外部発表Yes

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Enantioselectivity
Derivatives
Cyclopentanes
Nucleophiles
Titanium
Esters
Carbon

ASJC Scopus subject areas

  • Inorganic Chemistry

これを引用

Kitagawa, O., Inoue, T., & Taguchi, T. (1996). Iodocarbocyclization reaction. Reviews on Heteroatom Chemistry, 15, 243-262.

Iodocarbocyclization reaction. / Kitagawa, Osamu; Inoue, Tadashi; Taguchi, Takeo.

:: Reviews on Heteroatom Chemistry, 巻 15, 1996, p. 243-262.

研究成果: Article

Kitagawa, O, Inoue, T & Taguchi, T 1996, 'Iodocarbocyclization reaction', Reviews on Heteroatom Chemistry, 巻. 15, pp. 243-262.
Kitagawa, Osamu ; Inoue, Tadashi ; Taguchi, Takeo. / Iodocarbocyclization reaction. :: Reviews on Heteroatom Chemistry. 1996 ; 巻 15. pp. 243-262.
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