Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde

Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde

<b> </b>A novel and safe reaction protocol for the enantioselective enamine-catalysed addition of acetaldehyde to nitroalkenes is presented; this protocol makes use of a safe acetaldehyde precursor to access important intermediates to Active Pharmaceutical Ingredients (APIs), and allows...

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Bibliographic Details
Main Authors: Giuliana Giorgianni, Valeria Nori, Andrea Baschieri, Laura Palombi, Armando Carlone
Format: Article
Language:English
Published: MDPI AG 2020-11-01
Series:Catalysts
Subjects:
acetaldehyde
asymmetric catalysis
Michael addition
organocatalysis
pregabalin
Online Access:https://www.mdpi.com/2073-4344/10/11/1296
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spelling doaj-e19553b03ab8453eaf8f1219bba5533c2020-11-25T04:05:09ZengMDPI AGCatalysts2073-43442020-11-01101296129610.3390/catal10111296Organocatalyzed Michael Addition to Nitroalkenes via Masked AcetaldehydeGiuliana Giorgianni0Valeria Nori1Andrea Baschieri2Laura Palombi3Armando Carlone4Department of Physical and Chemical Sciences, Università degli Studi dell’Aquila, via Vetoio, 67100 L’Aquila, ItalyDepartment of Physical and Chemical Sciences, Università degli Studi dell’Aquila, via Vetoio, 67100 L’Aquila, ItalyDepartment of Physical and Chemical Sciences, Università degli Studi dell’Aquila, via Vetoio, 67100 L’Aquila, ItalyDepartment of Physical and Chemical Sciences, Università degli Studi dell’Aquila, via Vetoio, 67100 L’Aquila, ItalyDepartment of Physical and Chemical Sciences, Università degli Studi dell’Aquila, via Vetoio, 67100 L’Aquila, Italy<b> </b>A novel and safe reaction protocol for the enantioselective enamine-catalysed addition of acetaldehyde to nitroalkenes is presented; this protocol makes use of a safe acetaldehyde precursor to access important intermediates to Active Pharmaceutical Ingredients (APIs), and allows the use of fewer equivalents of acetaldehyde and lower catalyst loadings. The reaction developed proved to be suitable to be performed on gram-scale and to produce key intermediates for the synthesis of pharmacologically active compounds such as pregabalin.https://www.mdpi.com/2073-4344/10/11/1296acetaldehydeasymmetric catalysisMichael additionorganocatalysispregabalin
collection DOAJ
language English
format Article
sources DOAJ
author Giuliana Giorgianni
Valeria Nori
Andrea Baschieri
Laura Palombi
Armando Carlone
spellingShingle Giuliana Giorgianni
Valeria Nori
Andrea Baschieri
Laura Palombi
Armando Carlone
Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde
Catalysts
acetaldehyde
asymmetric catalysis
Michael addition
organocatalysis
pregabalin
author_facet Giuliana Giorgianni
Valeria Nori
Andrea Baschieri
Laura Palombi
Armando Carlone
author_sort Giuliana Giorgianni
title Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde
title_short Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde
title_full Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde
title_fullStr Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde
title_full_unstemmed Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde
title_sort organocatalyzed michael addition to nitroalkenes via masked acetaldehyde
publisher MDPI AG
series Catalysts
issn 2073-4344
publishDate 2020-11-01
description <b> </b>A novel and safe reaction protocol for the enantioselective enamine-catalysed addition of acetaldehyde to nitroalkenes is presented; this protocol makes use of a safe acetaldehyde precursor to access important intermediates to Active Pharmaceutical Ingredients (APIs), and allows the use of fewer equivalents of acetaldehyde and lower catalyst loadings. The reaction developed proved to be suitable to be performed on gram-scale and to produce key intermediates for the synthesis of pharmacologically active compounds such as pregabalin.
topic acetaldehyde
asymmetric catalysis
Michael addition
organocatalysis
pregabalin
url https://www.mdpi.com/2073-4344/10/11/1296
work_keys_str_mv AT giulianagiorgianni organocatalyzedmichaeladditiontonitroalkenesviamaskedacetaldehyde
AT valerianori organocatalyzedmichaeladditiontonitroalkenesviamaskedacetaldehyde
AT andreabaschieri organocatalyzedmichaeladditiontonitroalkenesviamaskedacetaldehyde
AT laurapalombi organocatalyzedmichaeladditiontonitroalkenesviamaskedacetaldehyde
AT armandocarlone organocatalyzedmichaeladditiontonitroalkenesviamaskedacetaldehyde
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