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

doi:10.1039/c5cc03659c

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 journal › Article › peer-review

18 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 language	English
Pages (from-to)	11229-11232
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	56
DOIs	https://doi.org/10.1039/c5cc03659c
Publication status	Published - 2015 Jul 18

ASJC Scopus subject areas

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

Access to Document

10.1039/c5cc03659c

Cite this

@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",

note = "Publisher Copyright: {\textcopyright} 2015 The Royal Society of Chemistry.",

year = "2015",

month = jul,

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

C2 - 26077702

AN - SCOPUS:84933555823

SN - 1359-7345

VL - 51

SP - 11229

EP - 11232

JO - Chemical Communications

JF - Chemical Communications

IS - 56

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this