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

doi:10.1016/j.tetlet.2014.11.040

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 + Show 4 more

https://doi.org/10.1016/j.tetlet.2014.11.040

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Journal: Tetrahedron Letters	Publication Date: Nov 18, 2014
Citations: 12

Affiliation: Tokyo University of Pharmacy and Life Sciences, Centrale Marseille, Aix-Marseille University, French National Centre for Scientific Research, Shibaura Institute of Technology

#Rotational Barrier #Chiral Axis + Show 8 more

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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 6kcal/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.

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