Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes

Zhonglin Tao, Kevin A. Robb, Kuo Zhao, Scott E Denmark

Research output: Contribution to journalArticle

Abstract

A sulfenium-ion-initiated, catalytic, enantioselective polyene cyclization is described. Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.

Original languageEnglish (US)
Pages (from-to)3569-3573
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number10
DOIs
StatePublished - Mar 14 2018

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Lewis Bases
Polyenes
Ions
ion
alkene
Enantioselectivity
Cyclization
Alkenes
Sulfides
Olefins
alcohol
Alcohols
Carbon
catalyst
Oxygen
oxygen
Catalysts
carbon

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes. / Tao, Zhonglin; Robb, Kevin A.; Zhao, Kuo; Denmark, Scott E.

In: Journal of the American Chemical Society, Vol. 140, No. 10, 14.03.2018, p. 3569-3573.

Research output: Contribution to journalArticle

Tao, Zhonglin ; Robb, Kevin A. ; Zhao, Kuo ; Denmark, Scott E. / Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes. In: Journal of the American Chemical Society. 2018 ; Vol. 140, No. 10. pp. 3569-3573.
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