Catalytic asymmetric hydrogenation of pyrimidines

Ryoichi Kuwano, Yuta Hashiguchi, Ryuhei Ikeda, Kentaro Ishizuka

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The asymmetric hydrogenation of pyrimidines proceeded with high enantioselectivity (up to 99% ee) using an iridium catalyst composed of [IrCl(cod)]2, a ferrocene-containing chiral diphosphine ligand (Josiphos), iodine, and Yb(OTf)3 (cod=1,5-cyclooctadiene). The chiral catalyst converted various 4-substituted pyrimidines into chiral 1,4,5,6-tetrahydropyrimidines in high yield. The lanthanide triflate is crucial for achieving the high enantioselectivity as well as for activating the heteroarene substrate.

Original languageEnglish
Pages (from-to)2393-2396
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number8
DOIs
Publication statusPublished - Feb 16 2015

Fingerprint

Pyrimidines
Enantioselectivity
Hydrogenation
Iridium
Lanthanoid Series Elements
Catalysts
Rare earth elements
Iodine
Ligands
Substrates
ferrocene
ytterbium(III) triflate
1,5-cyclooctadiene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Catalytic asymmetric hydrogenation of pyrimidines. / Kuwano, Ryoichi; Hashiguchi, Yuta; Ikeda, Ryuhei; Ishizuka, Kentaro.

In: Angewandte Chemie - International Edition, Vol. 54, No. 8, 16.02.2015, p. 2393-2396.

Research output: Contribution to journalArticle

Kuwano, Ryoichi ; Hashiguchi, Yuta ; Ikeda, Ryuhei ; Ishizuka, Kentaro. / Catalytic asymmetric hydrogenation of pyrimidines. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54, No. 8. pp. 2393-2396.
@article{075badb028b84b09b4282c4195dfd1e3,
title = "Catalytic asymmetric hydrogenation of pyrimidines",
abstract = "The asymmetric hydrogenation of pyrimidines proceeded with high enantioselectivity (up to 99{\%} ee) using an iridium catalyst composed of [IrCl(cod)]2, a ferrocene-containing chiral diphosphine ligand (Josiphos), iodine, and Yb(OTf)3 (cod=1,5-cyclooctadiene). The chiral catalyst converted various 4-substituted pyrimidines into chiral 1,4,5,6-tetrahydropyrimidines in high yield. The lanthanide triflate is crucial for achieving the high enantioselectivity as well as for activating the heteroarene substrate.",
author = "Ryoichi Kuwano and Yuta Hashiguchi and Ryuhei Ikeda and Kentaro Ishizuka",
year = "2015",
month = "2",
day = "16",
doi = "10.1002/anie.201410607",
language = "English",
volume = "54",
pages = "2393--2396",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "8",

}

TY - JOUR

T1 - Catalytic asymmetric hydrogenation of pyrimidines

AU - Kuwano, Ryoichi

AU - Hashiguchi, Yuta

AU - Ikeda, Ryuhei

AU - Ishizuka, Kentaro

PY - 2015/2/16

Y1 - 2015/2/16

N2 - The asymmetric hydrogenation of pyrimidines proceeded with high enantioselectivity (up to 99% ee) using an iridium catalyst composed of [IrCl(cod)]2, a ferrocene-containing chiral diphosphine ligand (Josiphos), iodine, and Yb(OTf)3 (cod=1,5-cyclooctadiene). The chiral catalyst converted various 4-substituted pyrimidines into chiral 1,4,5,6-tetrahydropyrimidines in high yield. The lanthanide triflate is crucial for achieving the high enantioselectivity as well as for activating the heteroarene substrate.

AB - The asymmetric hydrogenation of pyrimidines proceeded with high enantioselectivity (up to 99% ee) using an iridium catalyst composed of [IrCl(cod)]2, a ferrocene-containing chiral diphosphine ligand (Josiphos), iodine, and Yb(OTf)3 (cod=1,5-cyclooctadiene). The chiral catalyst converted various 4-substituted pyrimidines into chiral 1,4,5,6-tetrahydropyrimidines in high yield. The lanthanide triflate is crucial for achieving the high enantioselectivity as well as for activating the heteroarene substrate.

UR - http://www.scopus.com/inward/record.url?scp=85027926634&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85027926634&partnerID=8YFLogxK

U2 - 10.1002/anie.201410607

DO - 10.1002/anie.201410607

M3 - Article

VL - 54

SP - 2393

EP - 2396

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 8

ER -