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
Publication statusPublished - 1999 Dec 10
Externally publishedYes

Fingerprint

Amides
Stereoselectivity
Addition reactions
Esters
pantolactone
oxalyl chloride

Keywords

  • Anilides
  • Asymmetric reaction
  • Atropisomerism
  • Resolution

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions. / Kitagawa, Osamu; Momose, Shu ichi; Fushimi, Yoshihisa; Taguchi, Takeo.

In: Tetrahedron Letters, Vol. 40, No. 50, 10.12.1999, p. 8827-8831.

Research output: Contribution to journalArticle

Kitagawa, Osamu ; Momose, Shu ichi ; Fushimi, Yoshihisa ; Taguchi, Takeo. / Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions. In: Tetrahedron Letters. 1999 ; Vol. 40, No. 50. pp. 8827-8831.
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