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

研究成果: Contribution to journalArticle査読

29 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)2821-2831
ページ数11
ジャーナルTetrahedron Asymmetry
16
16
DOI
出版ステータス出版済み - 8 22 2005

All Science Journal Classification (ASJC) codes

  • 触媒
  • 物理化学および理論化学
  • 有機化学
  • 無機化学

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