Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one

Yuya Suzuki, Isao Takahashi, Yasuo Dobashi, Hiroshi Hasegawa, Christian Roussel, Osamu Kitagawa

Research output: Contribution to journalArticle

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Abstract

The rotational barrier around the N-C chiral axis in N-(2-tert-butylphenyl)-3,4-dihydrobenzoquinolin-2-one was found to be 6 kcal/mol lower than that in N-(2-tert-butylphenyl)-3,4-dihydroquinolin-2-one. X-ray crystal structures and 1H NMR spectra of both compounds indicate that the significant decrease in the rotational barrier in benzoquinolinone is brought about by destabilization of the ground state which is highlighted by a considerable distortion of the N-C chiral axis.

Original languageEnglish
Pages (from-to)132-135
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number1
DOIs
Publication statusPublished - 2015 Jan 1

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Keywords

  • Amination
  • Axially chiral
  • Distortion
  • Quinolinone
  • Rotational barrier

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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