Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition

Giada Arena, Chia-Chun Chen, Daniele Leonori*, Varinder K. Aggarwal

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

39 Citations (Scopus)
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Abstract

3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

Original languageEnglish
Pages (from-to)4250-4253
Number of pages4
JournalOrganic Letters
Volume15
Issue number16
Early online date2 Aug 2013
DOIs
Publication statusPublished - 16 Aug 2013

Keywords

  • CHIRAL NITRIDOMANGANESE COMPLEX
  • HIGHLY SUBSTITUTED PYRROLIDINES
  • CATALYZED CASCADE REACTIONS
  • EXCITATORY AMINO-ACIDS
  • ENE-TYPE REACTIONS
  • ACTIVATED OLEFINS
  • ENANTIOSELECTIVE SYNTHESIS
  • ASYMMETRIC-SYNTHESIS
  • KAINIC ACID
  • (+/-)-ALPHA-ALLOKAINIC ACID

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