Synthesis and stereochemical stability of new atropisomeric 1-(substituted phenyl)pyrrole derivatives

F. Faigl, G. Tárkányi, Katalin Fogassy, Dóra Tepfenhardt, Angelika Thurner

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Addition of organometallic reagents to optically active methyl 1-(2-methoxycarbonyl-6-trifluoromethylphenyl)pyrrole-2-carboxylate provided the corresponding tetrasubstituted diols and/or pyrrolo[1,2-a]benzoxazepines as pure enantiomers or racemates depending on the organometallic reagents used. Rotational energy barriers around the interconnecting C-N bonds were estimated by molecular modeling calculations and NMR measurements with the aim of clarifying the stereochemical stability order of the new atropisomeric compounds. NMR methods for the determination of the enantiomeric purity of the new compounds are proposed.

Original languageEnglish
Pages (from-to)1371-1377
Number of pages7
JournalTetrahedron
Volume64
Issue number7
DOIs
Publication statusPublished - Feb 11 2008

Fingerprint

Pyrroles
Organometallics
Nuclear magnetic resonance
Derivatives
Molecular modeling
Enantiomers
Energy barriers
2-pyrrolecarboxylic acid

Keywords

  • 1-Arylpyrroles
  • Atropisomers
  • Organometallics
  • Rotational energy
  • Stereochemical stability

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and stereochemical stability of new atropisomeric 1-(substituted phenyl)pyrrole derivatives. / Faigl, F.; Tárkányi, G.; Fogassy, Katalin; Tepfenhardt, Dóra; Thurner, Angelika.

In: Tetrahedron, Vol. 64, No. 7, 11.02.2008, p. 1371-1377.

Research output: Contribution to journalArticle

Faigl, F. ; Tárkányi, G. ; Fogassy, Katalin ; Tepfenhardt, Dóra ; Thurner, Angelika. / Synthesis and stereochemical stability of new atropisomeric 1-(substituted phenyl)pyrrole derivatives. In: Tetrahedron. 2008 ; Vol. 64, No. 7. pp. 1371-1377.
@article{937057a1fa6f494bac7b410d220c3d4e,
title = "Synthesis and stereochemical stability of new atropisomeric 1-(substituted phenyl)pyrrole derivatives",
abstract = "Addition of organometallic reagents to optically active methyl 1-(2-methoxycarbonyl-6-trifluoromethylphenyl)pyrrole-2-carboxylate provided the corresponding tetrasubstituted diols and/or pyrrolo[1,2-a]benzoxazepines as pure enantiomers or racemates depending on the organometallic reagents used. Rotational energy barriers around the interconnecting C-N bonds were estimated by molecular modeling calculations and NMR measurements with the aim of clarifying the stereochemical stability order of the new atropisomeric compounds. NMR methods for the determination of the enantiomeric purity of the new compounds are proposed.",
keywords = "1-Arylpyrroles, Atropisomers, Organometallics, Rotational energy, Stereochemical stability",
author = "F. Faigl and G. T{\'a}rk{\'a}nyi and Katalin Fogassy and D{\'o}ra Tepfenhardt and Angelika Thurner",
year = "2008",
month = "2",
day = "11",
doi = "10.1016/j.tet.2007.11.058",
language = "English",
volume = "64",
pages = "1371--1377",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "7",

}

TY - JOUR

T1 - Synthesis and stereochemical stability of new atropisomeric 1-(substituted phenyl)pyrrole derivatives

AU - Faigl, F.

AU - Tárkányi, G.

AU - Fogassy, Katalin

AU - Tepfenhardt, Dóra

AU - Thurner, Angelika

PY - 2008/2/11

Y1 - 2008/2/11

N2 - Addition of organometallic reagents to optically active methyl 1-(2-methoxycarbonyl-6-trifluoromethylphenyl)pyrrole-2-carboxylate provided the corresponding tetrasubstituted diols and/or pyrrolo[1,2-a]benzoxazepines as pure enantiomers or racemates depending on the organometallic reagents used. Rotational energy barriers around the interconnecting C-N bonds were estimated by molecular modeling calculations and NMR measurements with the aim of clarifying the stereochemical stability order of the new atropisomeric compounds. NMR methods for the determination of the enantiomeric purity of the new compounds are proposed.

AB - Addition of organometallic reagents to optically active methyl 1-(2-methoxycarbonyl-6-trifluoromethylphenyl)pyrrole-2-carboxylate provided the corresponding tetrasubstituted diols and/or pyrrolo[1,2-a]benzoxazepines as pure enantiomers or racemates depending on the organometallic reagents used. Rotational energy barriers around the interconnecting C-N bonds were estimated by molecular modeling calculations and NMR measurements with the aim of clarifying the stereochemical stability order of the new atropisomeric compounds. NMR methods for the determination of the enantiomeric purity of the new compounds are proposed.

KW - 1-Arylpyrroles

KW - Atropisomers

KW - Organometallics

KW - Rotational energy

KW - Stereochemical stability

UR - http://www.scopus.com/inward/record.url?scp=37649033197&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37649033197&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2007.11.058

DO - 10.1016/j.tet.2007.11.058

M3 - Article

AN - SCOPUS:37649033197

VL - 64

SP - 1371

EP - 1377

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 7

ER -