Enantioselective biomimetic polyene cyclization of polyprenoids Long-sought enantioselective reaction induced by a "chiral halonium ion"

Akira Sakakura, Kazuaki Ishihara

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Enantioselective biomimetic polyene cyclizations of polyprenoids have been studied for a long time. Very recently, we have developed the first "chiral iodonium ion"-induced enantioselective polyene cyclization of polyprenoids using a nucleophilic promoter. Achiral nucleophilic phosphorus compounds catalytically promote the diastereoselective halocyclization in dichloromethane to give a halogenated cyclic product in excellent yield. Moreover, chiral phosphoramidites stoichiometrically promote the enantioselective halocyclization of simple polyprenoids with N-iodosuccinimide in toluene to give iodinated cyclic products in up to 99 percent ee and 99 percent ds. Some enantioselective polycyclizations have been reported in addition to this halocyclization. One of the advantages of these biomimetic polycyclizations is the simultaneous formation of several carbon-carbon bonds with the relative and absolute stereocontrol. Enantioselective biomimetic domino reactions would be highly useful for the practical synthesis of natural products and related compounds.

Original languageEnglish
Pages (from-to)9-12
Number of pages4
JournalChimica Oggi
Volume25
Issue number5 SUPPL. 2
Publication statusPublished - 2007
Externally publishedYes

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Polyenes
Biomimetics
Cyclization
Ions
Carbon
Phosphorus Compounds
Methylene Chloride
Toluene
Biological Products

ASJC Scopus subject areas

  • Chemistry(all)
  • Biotechnology

Cite this

Enantioselective biomimetic polyene cyclization of polyprenoids Long-sought enantioselective reaction induced by a "chiral halonium ion". / Sakakura, Akira; Ishihara, Kazuaki.

In: Chimica Oggi, Vol. 25, No. 5 SUPPL. 2, 2007, p. 9-12.

Research output: Contribution to journalArticle

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