Stereoselective synthesis of diastereomeric atropisomeric lactam with various ring sizes and their structural characterization

Osamu Kitagawa, M. Fujita, M. Kohriyama, H. Hasegawa, T. Taguchi

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Diastereomeric atropisomeric N-ortho-tert-butylphenyl lactams with ring sizes from four to seven were prepared with high diastereoselectivity through an aminocyclization reaction. In the case of four- and five-membered ring formation, thermodynamically stable atropisomeric lactams having a trans-relationship between the ortho-tert-butyl group and the C-4 or C-5 substituent were obtained, while in the six- and seven-membered ring-forming reaction, cis-atropisomeric lactams, kinetic controlled products, were exclusively isolated. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)8539-8544
Number of pages6
JournalTetrahedron Letters
Volume41
Issue number44
Publication statusPublished - 2000 Oct 28
Externally publishedYes

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Lactams
Kinetics

Keywords

  • Atropisomerism
  • Diastereoselection
  • Isomerization
  • Lactam

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective synthesis of diastereomeric atropisomeric lactam with various ring sizes and their structural characterization. / Kitagawa, Osamu; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T.

In: Tetrahedron Letters, Vol. 41, No. 44, 28.10.2000, p. 8539-8544.

Research output: Contribution to journalArticle

Kitagawa, Osamu ; Fujita, M. ; Kohriyama, M. ; Hasegawa, H. ; Taguchi, T. / Stereoselective synthesis of diastereomeric atropisomeric lactam with various ring sizes and their structural characterization. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 44. pp. 8539-8544.
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AU - Taguchi, T.

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