Stereoselective synthesis of pinane-based β- And γ-amino acids via conjugate addition of lithium amides and nitromethane

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Abstract

Michael addition of dibenzylamine to (-)- and (+)-tert-butyl myrtenate, (-)-2 and (+)-2, derived from (-)- and (+)-myrtenal, furnished monoterpene-based β-amino acid derivatives in highly stereospecific reactions. The resultant amino esters (-)-3 and (+)-3 were transformed to unsubstituted, mono- and disubstituted and Fmoc-protected amino acids (-)-6-11 and (+)-6-11, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles. The microwave-assisted conjugate addition of nitromethane to α,β-unsaturated esters (-)-12 and (+)-12 likewise resulted in nitro esters (-)-13 and (+)-13 in highly stereospecific reactions. Compounds (-)-13 and (+)-13 were successfully transformed into γ-amino acids (-)-16 and (+)-16 in two steps.

Original languageEnglish
Pages (from-to)2498-2504
Number of pages7
JournalTetrahedron Asymmetry
Volume21
Issue number20
DOIs
Publication statusPublished - Oct 28 2010

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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