Este archivo ha sido creado el [07/11/224] por [Rocío Recio Jiménez]
 

GENERAL INFORMATION
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1. Dataset title:Stereoselective Synthesis of Chiral C2-Symmetric 1,3- and 1,5-Bissulfoxides
Guided by Horeau Principle: Understanding the Influence of the Carbon Chain Nature in its Ability for Metal Coordination [Dataset]


2. Authorship:

	Name: Moreno-Rodríguez, Nazaret
	Institution: University of Seville
	Email: nmoreno4@us.es
	ORCID:https://orcid.org/0000-0002-8702-6822  

	Name: Prieto, L. Alberto
	Institution: University of Seville
	Email: lprieto1@us.es
	ORCID:https://orcid.org/0000-0002-2172-6172

	Name: Valdivia, Victoria
	Institution: University of Seville
	Email: vvaldivia@us.es
	ORCID:https://orcid.org/0000-0003-3534-7074

	Name: Recio, Rocío
	Institution: University of Seville
	Email: rrecioj@us.es
	ORCID:https://orcid.org/0000-0002-7956-5295

	Name: Fernández, Inmaculada
	Institution: University of Seville
	Email: inmaff@us.es
	ORCID:https://orcid.org/0000-0002-3468-387X

DESCRIPTION
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1. Dataset language: English


2. Abstract:
Diastereomeric excess determination of 1,3-bisulfinates. 
Experimental data of 1,3-bis-(sulfinyl)propanes. 
Experimental data of allylation of N-(benzoyl)isobutylhydrazone. 
Experimental data of vinyl sulfoxides. 
Experimental data of 1,5-bis(sulfinyl)-3-thioderivatives. 
Figures of regioselective oxidation of 1,5-bis(sulfinyl)-3-thioderivatives.
Figures of palladium(II) and ruthenium(II) complexes formation.
HPLC chromatograms of selected compounds.
1H NMR, 13C{1H} NMR and 19F NMR of selected compounds.
2D NMR of selected compounds. 
X-ray Structural Analysis for (CDCC 2309479).


3. Keywords: 

Síntesis estereoselectiva; Ley de Horeau; Ligandos quirales C2 simétricos; bis-sulfóxidos
Stereoselective Synthesis; Horeau Principle; Chiral C2‑Symmetric ligands; Bis- Sulfoxides

4. Date of data collection: 17-07-2024

5. Publication Date: 06-11-2024

6. Grant information:

	Grant Agency:Consejería de Economía, Conocimiento, Empresas y Universidad, Junta de Andalucía (European Regional Development Fund (ERDF))
	Grant Number:US-1381590

	Grant Agency:Ministerio  de Ciencia, Innovación y Universidades (European Regional Development Fund (ERDF))
	Grant Number: PID2019-104767RB-I00



ACCESS INFORMATION
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1. Creative Commons License of the dataset: Licencia CC BY-NC-ND 

2. Dataset DOI:10.12795/11441/165883

3. Related publication: Moreno Rodríguez, N., Prieto Ramírez, L.A., Valdivia Giménez, V.E., Recio Jiménez, R. y Fernández Fernández, I. (2024). Stereoselective Synthesis of Chiral C2-Symmetric 1,3- and 1,5-Bis-Sulfoxides Guided by the Horeau Principle: Understanding the Influence of the Carbon Chain Nature in Its Ability for Metal Coordination. The Journal of Organic Chemistry, 89 (20), 15048-15061. https://doi.org/10.1021/acs.joc.4c01729.

4. Link to related datasets:  PMCID# PMC11494659


VERSIONING AND PROVENANCE
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1. Were data derived from another source?: Sí  J. Org. Chem. 2024, 89, 15048−15061.doi: 10.1021/acs.joc.4c01729


METHODOLOGICAL INFORMATION
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1. Information about instruments, calibration and standards:

All reactions were run under an atmosphere of dry argon using oven dried glassware and dried solvents. MeOH, toluene, THF, DMF, CH2Cl2, diethyl ether, were dried using molecular sieves, and highest quality solvents were used. Chemicals were obtained from commercial sources and were used without further purification. TLC was carried out on silica gel GF254 (Merck), and compounds were detected by charring with phosphomolybdic acid/EtOH. For flash chromatography, Merck 230–400 mesh silica gel was used. Chromatographic columns were eluted with a positive pressure of air, and eluents are given as volume-to-volume ratios (v/v). NMR spectra were recorded with Bruker Avance 300 and 500 MHz spectrometers. Chemical shifts are reported in ppm, and coupling constants are reported in Hz. Routine 1H and 13C spectra were referenced to the residual proton or carbon signals of the solvent, respectively. High-resolution mass spectra (HRMS) were recorded with a Kratos MS-80RFA 241-MC apparatus. Optical rotations were determined with a Perkin–Elmer 341 polarimeter. Melting points were measured with a Stuart SMP3 apparatus in open-ended capillary tubes. Methyl, p-tolyl and tert-butyl sulfinyl chlorides were obtained by the method reported by Herrmann[29] and Ellman. p-toluenesulfinates 32(RS) and 32(SS), and optically pure alkanesulfinates 23(RS), 23(SS), 24(RS), 24(SS) were prepared as previously described following DAG methodology. Menthyl p-toluenesulfinate 22(SS) was prepared as described by Solladiè. 

FILE OVERVIEW 
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1. Explain the file naming conversion, si es aplicable: ChiralC2Symmetricligands.pdf

El nombre se basa en el contenido del documento 


2. File list:

	File name:ChiralC2Symmetricligands.pdf
	Description: procedimientos sintéticos, de RMN y RX 


3. File format: PDF