Asymmetric inverse electron-demand 1,3-dipolar cycloaddition of ynolates with a chiral nitrone derived from L-serine leading to β-amino acid derivatives

Mitsuru Shindo, Keiko Ohtsuki, Kozo Shishido

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Abstract

Asymmetric 1,3-dipolar cycloaddition of lithium ynolates with a nitrone derived from Garner's aldehyde is described. The cycloadducts, 5-isoxazolidinones, were obtained in good yields with high diastereoselectivity. Alkylation of the intermediates, the 5-isoxazolidinone enolates, was also achieved with high selectivity, the products of which were converted into the enantiomerically pure β-amino acids, β-lactams, and γ-lactams. In our cycloaddition, lithium ynolates proved to be much better as nucleophiles than lithium enolates.

Original languageEnglish
Pages (from-to)2821-2831
Number of pages11
JournalTetrahedron Asymmetry
Volume16
Issue number16
DOIs
Publication statusPublished - Aug 22 2005

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All Science Journal Classification (ASJC) codes

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

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