Concise synthesis of C2-symmetric trans-2,5-dioxymethylpyrrolidine derivatives by novel cyclization

Seiichi Takano, Minoru Moriya, Yoshiharu Iwabuchi, Kunio Ogasawara

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

Treatment of (S)-1-benzyloxy-2-benzoylaminohex-5-ene with iodine in aqueous acetonitrile furnished (2S,5S)-5-benzoyloxymethyl-2-benzyloxymethylpyrroliaine stereoselectively in a single step. The product was converted into C2-symmetric (2S,5S)-2,5-dioxymethylpyrrolidines potentially utilizable as chiral auxiliaries and (2S,5S)-(-)-pyrrolidine-2,5-dicarboxylic acid isolated from marine alga Schizymenia dubyi.

Original languageEnglish
Pages (from-to)3805-3806
Number of pages2
JournalTetrahedron Letters
Volume30
Issue number29
DOIs
Publication statusPublished - 1989

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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