Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

Osamu Kitagawa, Shu ichi Momose, Yoshihisa Fushimi, Takeo Taguchi

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

Various atropisomeric amides were prepared in optically pure forms (≥98% ee) through the optical resolution of the amide ester derived from (R)-pantolactone, N-allyl-ortho-tert-butylaniline and oxalyl chloride. Asymmetric carbonyl addition reaction of an alkyllithium and asymmetric iodolactonization with these atropisomeric amides proceeded with high stereoselectivity.

Original languageEnglish
Pages (from-to)8827-8831
Number of pages5
JournalTetrahedron Letters
Volume40
Issue number50
DOIs
Publication statusPublished - 1999 Dec 10

Keywords

  • Anilides
  • Asymmetric reaction
  • Atropisomerism
  • Resolution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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