Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides

Osamu Kitagawa, Shu Ichi Momose, Yoichiro Yamada, Motoo Shiro, Takeo Taguchi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Treatment of chiral α-benzyloxy- or α-propargyloxycarboxamide with tert-BuLi gave β-hydroxycarboxamides (aldol derivatives) in high optical purity through the formation of α-lithiated ethers and the subsquent 1,2-Wittig rearrangement.

Original languageEnglish
Pages (from-to)4865-4868
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number29
DOIs
Publication statusPublished - 2001 Jul 16

Keywords

  • Aldols
  • Asymmetric reaction
  • Hydroxy acids and derivatives
  • Wittig rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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