Enantioselective Formal [3+2] Cycloaddition of Epoxides with Imines under Brønsted Base Catalysis: Synthesis of 1,3-Oxazolidines with Quaternary Stereogenic Center

Azusa Kondoh, Shiori Akahira, Masafumi Oishi, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

The formal [3+2] cycloaddition of epoxides and unsaturated compounds is a powerful methodology for the synthesis of densely functionalized five-membered heterocyclic compounds containing oxygen. Described is a novel enantioselective formal [3+2] cycloaddition of epoxides under Brønsted base catalysis. The bis(guanidino)iminophosphorane as a chiral organosuperbase catalyst enabled the enantioselective reaction of β,γ-epoxysulfones with imines, owing to its strong basicity and high stereocontrolling ability, to provide enantioenriched 1,3-oxazolidines having two stereogenic centers, including a quaternary one, in a highly diastereo- and enantioselective manner.

Original languageEnglish
Pages (from-to)6299-6303
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number21
DOIs
Publication statusPublished - 2018 May 22

Keywords

  • Brønsted base
  • asymmetric catalysis
  • cycloaddition
  • heterocycles
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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