The synthesis of optically active N-C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor

Yuya Suzuki, Masato Kageyama, Ryuichi Morisawa, Yasuo Dobashi, Hiroshi Hasegawa, Satoshi Yokojima, Osamu Kitagawa

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Optically active atropisomeric N-(2,5-di-tert-butylphenyl)-1,2,3,4-tetrahydroquinoline with an N-C chiral axis was prepared via a catalytic enantioselective reaction. The addition of methane sulfonic acid to this axially chiral quinoline dramatically lowered the barrier to rotation around the chiral axis.

Original languageEnglish
Pages (from-to)11229-11232
Number of pages4
JournalChemical Communications
Volume51
Issue number56
DOIs
Publication statusPublished - 2015 Jul 18

Fingerprint

Sulfonic Acids
Methane
Rotors
Acids
1,2,3,4-tetrahydroquinoline
quinoline

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Ceramics and Composites
  • Electronic, Optical and Magnetic Materials
  • Surfaces, Coatings and Films
  • Materials Chemistry
  • Metals and Alloys

Cite this

The synthesis of optically active N-C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor. / Suzuki, Yuya; Kageyama, Masato; Morisawa, Ryuichi; Dobashi, Yasuo; Hasegawa, Hiroshi; Yokojima, Satoshi; Kitagawa, Osamu.

In: Chemical Communications, Vol. 51, No. 56, 18.07.2015, p. 11229-11232.

Research output: Contribution to journalArticle

Suzuki, Yuya ; Kageyama, Masato ; Morisawa, Ryuichi ; Dobashi, Yasuo ; Hasegawa, Hiroshi ; Yokojima, Satoshi ; Kitagawa, Osamu. / The synthesis of optically active N-C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor. In: Chemical Communications. 2015 ; Vol. 51, No. 56. pp. 11229-11232.
@article{209b63fd9caa4210aecc01e0ea055328,
title = "The synthesis of optically active N-C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor",
abstract = "Optically active atropisomeric N-(2,5-di-tert-butylphenyl)-1,2,3,4-tetrahydroquinoline with an N-C chiral axis was prepared via a catalytic enantioselective reaction. The addition of methane sulfonic acid to this axially chiral quinoline dramatically lowered the barrier to rotation around the chiral axis.",
author = "Yuya Suzuki and Masato Kageyama and Ryuichi Morisawa and Yasuo Dobashi and Hiroshi Hasegawa and Satoshi Yokojima and Osamu Kitagawa",
year = "2015",
month = "7",
day = "18",
doi = "10.1039/c5cc03659c",
language = "English",
volume = "51",
pages = "11229--11232",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "56",

}

TY - JOUR

T1 - The synthesis of optically active N-C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor

AU - Suzuki, Yuya

AU - Kageyama, Masato

AU - Morisawa, Ryuichi

AU - Dobashi, Yasuo

AU - Hasegawa, Hiroshi

AU - Yokojima, Satoshi

AU - Kitagawa, Osamu

PY - 2015/7/18

Y1 - 2015/7/18

N2 - Optically active atropisomeric N-(2,5-di-tert-butylphenyl)-1,2,3,4-tetrahydroquinoline with an N-C chiral axis was prepared via a catalytic enantioselective reaction. The addition of methane sulfonic acid to this axially chiral quinoline dramatically lowered the barrier to rotation around the chiral axis.

AB - Optically active atropisomeric N-(2,5-di-tert-butylphenyl)-1,2,3,4-tetrahydroquinoline with an N-C chiral axis was prepared via a catalytic enantioselective reaction. The addition of methane sulfonic acid to this axially chiral quinoline dramatically lowered the barrier to rotation around the chiral axis.

UR - http://www.scopus.com/inward/record.url?scp=84933555823&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84933555823&partnerID=8YFLogxK

U2 - 10.1039/c5cc03659c

DO - 10.1039/c5cc03659c

M3 - Article

VL - 51

SP - 11229

EP - 11232

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 56

ER -