Three-component reactions with (S)-methyl pyroglutamate: An efficient way to diversely substituted asymmetric amidocyclohexenes

Sandra Hübner, Dirk Michalik, Haijun Jiao, Helfried Neumann, Stefan Klaus, Dirk Strübing, Anke Spannenberg, Matthias Beller

Research output: Contribution to journalReview articlepeer-review

12 Scopus citations

Abstract

Chiral N-dienyl lactams are crucial building blocks for the synthesis of complex organic compounds. However, their generation is rather challenging. This paper reports the novel one-pot reaction of (S)-methyl pyroglutamate as the amide component with different aldehydes and dienophiles (AAD reaction) to give novel chiral 1-amido-2-cyclohexenes. The corresponding N-dienyl lactams generated in situ undergo subsequent Diels-Alder reactions in good yield and diastereoselectivity. The scope and limitations of the three-component protocol were investigated. X-ray and NMR spectroscopic analysis of the products as well as DFT calculations of the intermediates were also performed to explain the observed stereoselectivity and structural features.

Original languageEnglish
Pages (from-to)734-746
Number of pages13
JournalChemistry - An Asian Journal
Volume2
Issue number6
DOIs
StatePublished - 2007
Externally publishedYes

Keywords

  • Chiral dienamides
  • Diastereoselectivity
  • Diels-Alder reactions
  • Multicomponent reactions
  • Pyroglutamate

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