μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols

Rikiya Horikawa, Chika Fujimoto, Ryo Yazaki, Takashi Ohshima

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A highly chemoselective and reactive μ-oxo-dinuclear iron(III) salen catalyst for transesterification was developed. The developed iron complex catalyzed acylation of aliphatic amino alcohols with nearly perfect O-selectivity, even when using activated esters, for which chemoselectivity is more difficult to control. In addition, O-selective transesterification of aromatic amino alcohols was achieved for the first time. The high activity of the iron complex enabled the use of sterically congested tertiary alcohols, including unprecedented tert-butanol.

Original languageEnglish
Pages (from-to)12278-12281
Number of pages4
JournalChemistry - A European Journal
Volume22
Issue number35
DOIs
Publication statusPublished - Jan 1 2016

Fingerprint

Amino alcohols
Amino Alcohols
Acylation
Transesterification
Alcohols
Iron
tert-Butyl Alcohol
Butenes
Esters
Catalysts

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols. / Horikawa, Rikiya; Fujimoto, Chika; Yazaki, Ryo; Ohshima, Takashi.

In: Chemistry - A European Journal, Vol. 22, No. 35, 01.01.2016, p. 12278-12281.

Research output: Contribution to journalArticle

@article{f10a5e55162a4d5bbfddcf31804379d9,
title = "μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols",
abstract = "A highly chemoselective and reactive μ-oxo-dinuclear iron(III) salen catalyst for transesterification was developed. The developed iron complex catalyzed acylation of aliphatic amino alcohols with nearly perfect O-selectivity, even when using activated esters, for which chemoselectivity is more difficult to control. In addition, O-selective transesterification of aromatic amino alcohols was achieved for the first time. The high activity of the iron complex enabled the use of sterically congested tertiary alcohols, including unprecedented tert-butanol.",
author = "Rikiya Horikawa and Chika Fujimoto and Ryo Yazaki and Takashi Ohshima",
year = "2016",
month = "1",
day = "1",
doi = "10.1002/chem.201602801",
language = "English",
volume = "22",
pages = "12278--12281",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "35",

}

TY - JOUR

T1 - μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols

AU - Horikawa, Rikiya

AU - Fujimoto, Chika

AU - Yazaki, Ryo

AU - Ohshima, Takashi

PY - 2016/1/1

Y1 - 2016/1/1

N2 - A highly chemoselective and reactive μ-oxo-dinuclear iron(III) salen catalyst for transesterification was developed. The developed iron complex catalyzed acylation of aliphatic amino alcohols with nearly perfect O-selectivity, even when using activated esters, for which chemoselectivity is more difficult to control. In addition, O-selective transesterification of aromatic amino alcohols was achieved for the first time. The high activity of the iron complex enabled the use of sterically congested tertiary alcohols, including unprecedented tert-butanol.

AB - A highly chemoselective and reactive μ-oxo-dinuclear iron(III) salen catalyst for transesterification was developed. The developed iron complex catalyzed acylation of aliphatic amino alcohols with nearly perfect O-selectivity, even when using activated esters, for which chemoselectivity is more difficult to control. In addition, O-selective transesterification of aromatic amino alcohols was achieved for the first time. The high activity of the iron complex enabled the use of sterically congested tertiary alcohols, including unprecedented tert-butanol.

UR - http://www.scopus.com/inward/record.url?scp=84982124140&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84982124140&partnerID=8YFLogxK

U2 - 10.1002/chem.201602801

DO - 10.1002/chem.201602801

M3 - Article

VL - 22

SP - 12278

EP - 12281

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 35

ER -