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

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

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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
DOIs
Publication statusPublished - 2000 Oct 28

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Keywords

  • Atropisomerism
  • Diastereoselection
  • Isomerization
  • Lactam

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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