Iodocarbocyclization reaction

Osamu Kitagawa, Tadashi Inoue, Takeo Taguchi

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)243-262
Number of pages20
JournalReviews on Heteroatom Chemistry
Volume15
Publication statusPublished - 1996
Externally publishedYes

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Keywords

  • Catalytic asymmetric reaction
  • Chiral ligand
  • Diastereoselective reaction
  • Iodine
  • Iodocarbocyclization reaction
  • Stereospecific reaction
  • Titanium alkoxide

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

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