Achiral 2-pyridone and 4-aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals

Arimasa Matsumoto; Daisuke Tateishi; Tsuyoshi Nakajima; Shiori Kurosaki; Tomohiro Ogawa; Tsuneomi Kawasaki; Kenso Soai

doi:10.1002/chir.23617

Achiral 2-pyridone and 4-aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals

Arimasa Matsumoto, Daisuke Tateishi, Tsuyoshi Nakajima, Shiori Kurosaki, Tomohiro Ogawa, Tsuneomi Kawasaki, Kenso Soai

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

Enantiomorphous crystals of achiral 2-pyridone and 4-aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5-pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine-5-carbaldehyde, that is, the Soai reaction. Following a significant amplification of enantiomeric excess through asymmetric autocatalysis, highly enantioenriched 5-pyrimidyl alkanol could be synthesized with their corresponding absolute configurations to those of chiral crystals of 2-pyridone and 4-aminopyridine.

Original language	English
Article number	e23617
Journal	Chirality
Volume	36
Issue number	1
DOIs	https://doi.org/10.1002/chir.23617
Publication status	Published - Jan 2024

Keywords

5-pyrimidyl alkanol
Soai reaction
aminopyridine
amplification of ee
asymmetric autocatalysis
chiral crystal
homochirality
origin of chirality
pyridone
pyrimidine-5-carbaldehyde

Access to Document

10.1002/chir.23617

Cite this

@article{2ac86632e0d94b2e85fc364f994755ca,

title = "Achiral 2-pyridone and 4-aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals",

abstract = "Enantiomorphous crystals of achiral 2-pyridone and 4-aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5-pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine-5-carbaldehyde, that is, the Soai reaction. Following a significant amplification of enantiomeric excess through asymmetric autocatalysis, highly enantioenriched 5-pyrimidyl alkanol could be synthesized with their corresponding absolute configurations to those of chiral crystals of 2-pyridone and 4-aminopyridine.",

keywords = "5-pyrimidyl alkanol, Soai reaction, aminopyridine, amplification of ee, asymmetric autocatalysis, chiral crystal, homochirality, origin of chirality, pyridone, pyrimidine-5-carbaldehyde",

author = "Arimasa Matsumoto and Daisuke Tateishi and Tsuyoshi Nakajima and Shiori Kurosaki and Tomohiro Ogawa and Tsuneomi Kawasaki and Kenso Soai",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Chirality published by Wiley Periodicals LLC.",

year = "2024",

month = jan,

doi = "10.1002/chir.23617",

language = "English",

volume = "36",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley-Liss Inc.",

number = "1",

}

TY - JOUR

T1 - Achiral 2-pyridone and 4-aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals

AU - Matsumoto, Arimasa

AU - Tateishi, Daisuke

AU - Nakajima, Tsuyoshi

AU - Kurosaki, Shiori

AU - Ogawa, Tomohiro

AU - Kawasaki, Tsuneomi

AU - Soai, Kenso

PY - 2024/1

Y1 - 2024/1

N2 - Enantiomorphous crystals of achiral 2-pyridone and 4-aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5-pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine-5-carbaldehyde, that is, the Soai reaction. Following a significant amplification of enantiomeric excess through asymmetric autocatalysis, highly enantioenriched 5-pyrimidyl alkanol could be synthesized with their corresponding absolute configurations to those of chiral crystals of 2-pyridone and 4-aminopyridine.

AB - Enantiomorphous crystals of achiral 2-pyridone and 4-aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5-pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine-5-carbaldehyde, that is, the Soai reaction. Following a significant amplification of enantiomeric excess through asymmetric autocatalysis, highly enantioenriched 5-pyrimidyl alkanol could be synthesized with their corresponding absolute configurations to those of chiral crystals of 2-pyridone and 4-aminopyridine.

KW - 5-pyrimidyl alkanol

KW - Soai reaction

KW - aminopyridine

KW - amplification of ee

KW - asymmetric autocatalysis

KW - chiral crystal

KW - homochirality

KW - origin of chirality

KW - pyridone

KW - pyrimidine-5-carbaldehyde

UR - http://www.scopus.com/inward/record.url?scp=85169077353&partnerID=8YFLogxK

U2 - 10.1002/chir.23617

DO - 10.1002/chir.23617

M3 - Article

C2 - 37621025

AN - SCOPUS:85169077353

SN - 0899-0042

VL - 36

JO - Chirality

JF - Chirality

IS - 1

M1 - e23617

ER -

Achiral 2-pyridone and 4-aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this