Aufsatz
Phospholanes via Twofold C-H-Addition to Phospholes
Zusammenfassung
A synthetic route towards phospholanes via twofold C−H-addition of a DMSO molecule to β-H substituted phospholes is described. The resulting fused phospholane oxothiolane system in case of symmetric α-substitution possesses four stereogenic centers or rather six in case of asymmetric α-substitution. The reaction conditions are shown to be applicable for a variety of phospholes with different P- or α-substituents always leading to stereoselective formation of the fused heterocyclic ring system. All phospholane derivatives with one exception are sufficiently air stable for purification with column chromatography and are fully characterized by NMR and elemental analysis and mass spectrometry. With the help of X-ray crystallography, the different configurations of the isomers could be demonstrated. For one model system derivatization reactions are presented. When oxidizing or reducing the sulfoxide group only a single diastereomer is observed.
Zitierform
In: Advanced Synthesis & Catalysis Volume 366 / Issue 12 (2024-05-23) , S. 2764-2774 ; eissn:1615-4169Förderhinweis
Gefördert im Rahmen des Projekts DEAL ; DFGZitieren
@article{doi:10.17170/kobra-2024072410576,
author={Getfert, Katharina and Roesler, Fabian and Bruhn, Clemens and Pietschnig, Rudolf},
title={Phospholanes via Twofold C-H-Addition to Phospholes},
journal={Advanced Synthesis & Catalysis},
year={2024}
}
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2024-07-24T11:21:59Z 2024-07-24T11:21:59Z 2024-05-23 doi:10.17170/kobra-2024072410576 http://hdl.handle.net/123456789/15935 Gefördert im Rahmen des Projekts DEAL ; DFG eng Namensnennung 4.0 International http://creativecommons.org/licenses/by/4.0/ addition reaction fused ring system phospholane phosphole X-ray crystallography 540 Phospholanes via Twofold C-H-Addition to Phospholes Aufsatz A synthetic route towards phospholanes via twofold C−H-addition of a DMSO molecule to β-H substituted phospholes is described. The resulting fused phospholane oxothiolane system in case of symmetric α-substitution possesses four stereogenic centers or rather six in case of asymmetric α-substitution. The reaction conditions are shown to be applicable for a variety of phospholes with different P- or α-substituents always leading to stereoselective formation of the fused heterocyclic ring system. All phospholane derivatives with one exception are sufficiently air stable for purification with column chromatography and are fully characterized by NMR and elemental analysis and mass spectrometry. With the help of X-ray crystallography, the different configurations of the isomers could be demonstrated. For one model system derivatization reactions are presented. When oxidizing or reducing the sulfoxide group only a single diastereomer is observed. open access Getfert, Katharina Roesler, Fabian Bruhn, Clemens Pietschnig, Rudolf doi:10.1002/adsc.202400288 DFG Grant Number: CRC 1319, ELCH Röntgenkristallographie Phospholane Additionsreaktion publishedVersion eissn:1615-4169 Issue 12 Advanced Synthesis & Catalysis 2764-2774 Volume 366 false
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