Versatile use of acid-catalyzed ring-opening of β-aziridinyl-α,β-enoates to stereoselective synthesis of peptidomimetics

Hirokazu Tamamura, Tomohiro Tanaka, Hiroshi Tsutsumi, Koji Nemoto, Satoko Mizokami, Nami Ohashi, Shinya Oishi, Nobutaka Fujii

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Treatment of N-arylsulfonylaziridines bearing α,β-unsaturated esters with alcohols, thiols or weak acids such as AcOH in the presence of catalytic amount of Lewis acids affords regio- and stereoselectively ring-opened products, such as δ-aminated γ-alkoxy-(alkylthio or acetoxy)-α,β-enoates. In addition, the regio- and stereoselective ring-opening reactions can be performed on solid supports and applied to stereoselective synthesis of (E)-alkene dipeptide isosteres.

Original languageEnglish
Pages (from-to)9243-9254
Number of pages12
JournalTetrahedron
Volume63
Issue number37
DOIs
Publication statusPublished - 10 Sep 2007

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