Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions

Béla Mátravölgyi, Szilvia Deák, Zsuzsanna Erdélyi, Tamás Hergert, Péter Ábrányi-Balogh, F. Faigl

Research output: Contribution to journalArticle

Abstract

Syntheses of two regioisomeric series of atropisomeric amino alcohols and a comparative study on their application in the enantio-selective addition of diethylzinc to benzaldehyde are reported. Systematic modification of the electronic and steric properties of the functional groups resulted in highly efficient catalyst ligands in both series. Quantum-chemical calculations agreed well with the experimental results of this first systematic comparative study on regioisomeric-atropisomeric ligands.

Original languageEnglish
Article numberst-2018-d0265-c
Pages (from-to)2171-2175
Number of pages5
JournalSynlett
Volume29
Issue number16
DOIs
Publication statusPublished - Jan 1 2018

Fingerprint

Amino Alcohols
Organometallics
Ligands
Functional groups
Catalysts
diethylzinc
benzaldehyde

Keywords

  • amino alcohols
  • asymmetric catalysis
  • atropisomerism
  • enantioselectivity
  • ligands
  • phenylpyrrole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions. / Mátravölgyi, Béla; Deák, Szilvia; Erdélyi, Zsuzsanna; Hergert, Tamás; Ábrányi-Balogh, Péter; Faigl, F.

In: Synlett, Vol. 29, No. 16, st-2018-d0265-c, 01.01.2018, p. 2171-2175.

Research output: Contribution to journalArticle

Mátravölgyi, Béla ; Deák, Szilvia ; Erdélyi, Zsuzsanna ; Hergert, Tamás ; Ábrányi-Balogh, Péter ; Faigl, F. / Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions. In: Synlett. 2018 ; Vol. 29, No. 16. pp. 2171-2175.
@article{5523ad6a3a054373b3fb6edebea381bf,
title = "Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions",
abstract = "Syntheses of two regioisomeric series of atropisomeric amino alcohols and a comparative study on their application in the enantio-selective addition of diethylzinc to benzaldehyde are reported. Systematic modification of the electronic and steric properties of the functional groups resulted in highly efficient catalyst ligands in both series. Quantum-chemical calculations agreed well with the experimental results of this first systematic comparative study on regioisomeric-atropisomeric ligands.",
keywords = "amino alcohols, asymmetric catalysis, atropisomerism, enantioselectivity, ligands, phenylpyrrole",
author = "B{\'e}la M{\'a}trav{\"o}lgyi and Szilvia De{\'a}k and Zsuzsanna Erd{\'e}lyi and Tam{\'a}s Hergert and P{\'e}ter {\'A}br{\'a}nyi-Balogh and F. Faigl",
year = "2018",
month = "1",
day = "1",
doi = "10.1055/s-0037-1610551",
language = "English",
volume = "29",
pages = "2171--2175",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "16",

}

TY - JOUR

T1 - Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions

AU - Mátravölgyi, Béla

AU - Deák, Szilvia

AU - Erdélyi, Zsuzsanna

AU - Hergert, Tamás

AU - Ábrányi-Balogh, Péter

AU - Faigl, F.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - Syntheses of two regioisomeric series of atropisomeric amino alcohols and a comparative study on their application in the enantio-selective addition of diethylzinc to benzaldehyde are reported. Systematic modification of the electronic and steric properties of the functional groups resulted in highly efficient catalyst ligands in both series. Quantum-chemical calculations agreed well with the experimental results of this first systematic comparative study on regioisomeric-atropisomeric ligands.

AB - Syntheses of two regioisomeric series of atropisomeric amino alcohols and a comparative study on their application in the enantio-selective addition of diethylzinc to benzaldehyde are reported. Systematic modification of the electronic and steric properties of the functional groups resulted in highly efficient catalyst ligands in both series. Quantum-chemical calculations agreed well with the experimental results of this first systematic comparative study on regioisomeric-atropisomeric ligands.

KW - amino alcohols

KW - asymmetric catalysis

KW - atropisomerism

KW - enantioselectivity

KW - ligands

KW - phenylpyrrole

UR - http://www.scopus.com/inward/record.url?scp=85053880677&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85053880677&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1610551

DO - 10.1055/s-0037-1610551

M3 - Article

VL - 29

SP - 2171

EP - 2175

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 16

M1 - st-2018-d0265-c

ER -