Heterocyclische Verbindungen aus Zuckern, XV

Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbonsäuren. Chiralitätstransfer auf C-3 in 3,4-Dihydro-1 H-pyrrolo[1,2-c]thiazolen

Translated title of the contribution: Heterocyclic compounds from sugars, XV: On the configuration of chiral C-2 substituted 1,3-thiazolidine-4-carboxylic acids. Chirality transfer to C-3 of 3,4-dihydro-1 H-pyrrolo[1,2-c]thiazoles

Z. Györgydeák, L. Szilágyi, J. Kajtár, G. Argay, A. Kálmán

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3+2]-cycloaddition reactions via mesoionic oxazolone ("münchnone") intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through1H- and CD-spectra and the molecular structure of (3 S)-3da has been determined by X-ray crystallography.

Original languageGerman
Pages (from-to)189-208
Number of pages20
JournalMonatshefte fur Chemie
Volume125
Issue number2
DOIs
Publication statusPublished - 1989

Fingerprint

Heterocyclic Compounds
Thiazoles
Chirality
Carboxylic Acids
Sugars
Oxazolone
Dicarboxylic Acids
Cycloaddition
X ray crystallography
Molecular structure
Esters
thiazolidine-4-carboxylic acid

Keywords

  • 3,4-Dihydro-1 H-pyrrolo[1,2-c]thiazoles
  • 4-Thiazolidine carboxylic acids
  • Chirality

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Heterocyclische Verbindungen aus Zuckern, XV: Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbons{\"a}uren. Chiralit{\"a}tstransfer auf C-3 in 3,4-Dihydro-1 H-pyrrolo[1,2-c]thiazolen",
abstract = "5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3+2]-cycloaddition reactions via mesoionic oxazolone ({"}m{\"u}nchnone{"}) intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through1H- and CD-spectra and the molecular structure of (3 S)-3da has been determined by X-ray crystallography.",
keywords = "3,4-Dihydro-1 H-pyrrolo[1,2-c]thiazoles, 4-Thiazolidine carboxylic acids, Chirality",
author = "Z. Gy{\"o}rgyde{\'a}k and L. Szil{\'a}gyi and J. Kajt{\'a}r and G. Argay and A. K{\'a}lm{\'a}n",
year = "1989",
doi = "10.1007/BF00818164",
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T1 - Heterocyclische Verbindungen aus Zuckern, XV

T2 - Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbonsäuren. Chiralitätstransfer auf C-3 in 3,4-Dihydro-1 H-pyrrolo[1,2-c]thiazolen

AU - Györgydeák, Z.

AU - Szilágyi, L.

AU - Kajtár, J.

AU - Argay, G.

AU - Kálmán, A.

PY - 1989

Y1 - 1989

N2 - 5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3+2]-cycloaddition reactions via mesoionic oxazolone ("münchnone") intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through1H- and CD-spectra and the molecular structure of (3 S)-3da has been determined by X-ray crystallography.

AB - 5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3+2]-cycloaddition reactions via mesoionic oxazolone ("münchnone") intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through1H- and CD-spectra and the molecular structure of (3 S)-3da has been determined by X-ray crystallography.

KW - 3,4-Dihydro-1 H-pyrrolo[1,2-c]thiazoles

KW - 4-Thiazolidine carboxylic acids

KW - Chirality

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