Cooperative activation with chiral nucleophilic catalysts and n-haloimides: Enantioselective iodolactonization of 4-arylmethyl-4-pentenoic acids

Hidefumi Nakatsuji, Yasuhiro Sawamura, Akira Sakakura, Kazuaki Ishihara

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78 Citations (Scopus)

Abstract

Chiral triaryl phosphates promote the enantioselective iodolactonization of 4-substituted 4-pentenoic acids to give the corresponding iodolactones in high yields with high enantioselectivity. N-Chlorophthalimide (NCP) is employed as a Lewis acidic activator and oxidant of I2 for the present iodolactonization. In combination with 1.5 equivalents of NCP, only 0.5 equivalents of I2 are sufficient to generate the iodinating reagent. Active duty: Chiral triaryl phosphates promote the enantioselective iodolactonization of 4-substituted 4-pentenoic acids to give the corresponding iodolactones in high yields with high enantioselectivity (see scheme). N-Chlorophthalimide (NCP) is employed as a Lewis acidic activator and oxidant of I2 for the present iodolactonization. In combination with 1.5 equivalents of NCP, only 0.5 equivalents of I2 are sufficient for generating the iodinating reagent.

Original languageEnglish
Pages (from-to)6974-6977
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number27
DOIs
Publication statusPublished - Jul 1 2014

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Keywords

  • asymmetric catalysis
  • cyclization
  • iodine
  • lactones
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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