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

18 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
Externally publishedYes

Fingerprint

Ethers
Chirality
Derivatives
3-hydroxybutanal

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides. / Kitagawa, Osamu; Momose, Shu Ichi; Yamada, Yoichiro; Shiro, Motoo; Taguchi, Takeo.

In: Tetrahedron Letters, Vol. 42, No. 29, 16.07.2001, p. 4865-4868.

Research output: Contribution to journalArticle

Kitagawa, Osamu ; Momose, Shu Ichi ; Yamada, Yoichiro ; Shiro, Motoo ; Taguchi, Takeo. / Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 29. pp. 4865-4868.
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