Enantiocontrolled synthesis of polychlorinated hydrocarbon motifs: A nucleophilic multiple chlorination process revisited

Takehiko Yoshimitsu, Naoya Fukumoto, Tetsuaki Tanaka

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

Polychlorinated hydrocarbon motifs have been synthesized in enantiomerically pure forms by means of nucleophilic multiple chlorinations of chiral epoxides, which stereospecifically incorporate halogen atoms into oxygenated molecular scaffolds. The present study demonstrates the scope of the N-chlorosuccinimide (NCS)/organophosphine reagent system that forms multiple sp3C-Cl bonds in a regularly repeating pattern with proper stereochemical configurations and evaluates its applicability to various epoxides having elaborate structures. It is noteworthy that tetrachlorinated motifs are produced in one step from bisepoxides by using NCS/Ph3P. Furthermore, Ph2PCl used in combination with NCS has been found to serve as a potentially useful alternative to NCS/Ph3P, especially for promoting dichlorination reactions of alkenyl-substituted epoxides.

Original languageEnglish
Pages (from-to)696-702
Number of pages7
JournalJournal of Organic Chemistry
Volume74
Issue number2
DOIs
Publication statusPublished - Jan 16 2009
Externally publishedYes

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Chlorination
Halogenation
Hydrocarbons
Epoxy Compounds
Halogens
Scaffolds
Atoms
N-chlorosuccinimide

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Enantiocontrolled synthesis of polychlorinated hydrocarbon motifs : A nucleophilic multiple chlorination process revisited. / Yoshimitsu, Takehiko; Fukumoto, Naoya; Tanaka, Tetsuaki.

In: Journal of Organic Chemistry, Vol. 74, No. 2, 16.01.2009, p. 696-702.

Research output: Contribution to journalArticle

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