Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers

The enantioselective hydrogenation of ethyl pyruvate using a Pt/SiO2 catalyst modified with six different chiral modifiers was studied. The chiral modifiers chosen were: (S)-(+)-1-aminoindan, (R)-(−)-1-aminoindan, (1R,2S)-(+)-cis-1- amino-2-indanol, (1S,2R)-(−)-cis-1-amino-2-indanol, (S)-(+)-1-indan...

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Detalles Bibliográficos
Autores principales:	Ruggera, José Fernando, Merlo, Andrea Beatriz, Pis Diez, Reinaldo, Casella, Mónica Laura
Formato:	Articulo Preprint
Lenguaje:	Inglés
Publicado:	2016
Materias:	Química Enantioselectivity Ethyl pyruvate Non-cinchona modifiers Dft Platinum
Acceso en línea:	http://sedici.unlp.edu.ar/handle/10915/104243 http://hdl.handle.net/11336/41639
Aporte de:	SEDICI (UNLP) de Universidad Nacional de La Plata

id	I19-R120-10915-104243
record_format	dspace
institution	Universidad Nacional de La Plata
institution_str	I-19
repository_str	R-120
collection	SEDICI (UNLP)
language	Inglés
topic	Química Enantioselectivity Ethyl pyruvate Non-cinchona modifiers Dft Platinum
spellingShingle	Química Enantioselectivity Ethyl pyruvate Non-cinchona modifiers Dft Platinum Ruggera, José Fernando Merlo, Andrea Beatriz Pis Diez, Reinaldo Casella, Mónica Laura Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
topic_facet	Química Enantioselectivity Ethyl pyruvate Non-cinchona modifiers Dft Platinum
description	The enantioselective hydrogenation of ethyl pyruvate using a Pt/SiO2 catalyst modified with six different chiral modifiers was studied. The chiral modifiers chosen were: (S)-(+)-1-aminoindan, (R)-(−)-1-aminoindan, (1R,2S)-(+)-cis-1- amino-2-indanol, (1S,2R)-(−)-cis-1-amino-2-indanol, (S)-(+)-1-indanol and (R)-(−)-1-indanol.An excess of the (R) enantiomer of the product of 63% and 45% with (S)-(+)-1-aminoindan and (R)-(−)-1-aminoindan modifiers, respectively was obtained. When using (1S,2R)-(−)-cis-1-amino-2-indanol and (1R,2S)-(+)-cis-1-amino-2-indanol, the enantiomeric excess (ee%) obtained was 30% and 5%, respectively, while with both indanols ee% did not exceed 8%. Molecular modeling of the complex formed between the chiral modifier and ethyl pyruvate performed by DFT calculations allowed predicting the values of ee% obtained experimentally. The low ee% value obtained both aminoindanol chiral modifiers were used, could be explained by the analysis of non-covalent interactions (NCI) method. These calculations demonstrated the presence of an intramolecular hydrogen bond in the structure of these modifiers.
format	Articulo Preprint
author	Ruggera, José Fernando Merlo, Andrea Beatriz Pis Diez, Reinaldo Casella, Mónica Laura
author_facet	Ruggera, José Fernando Merlo, Andrea Beatriz Pis Diez, Reinaldo Casella, Mónica Laura
author_sort	Ruggera, José Fernando
title	Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_short	Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_full	Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_fullStr	Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_full_unstemmed	Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_sort	experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a pt catalyst with new non-cinchona chiral modifiers
publishDate	2016
url	http://sedici.unlp.edu.ar/handle/10915/104243 http://hdl.handle.net/11336/41639
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bdutipo_str	Repositorios
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Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers

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