Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde
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 equ...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-11-01
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| Series: | Catalysts |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4344/10/11/1296 |
| _version_ | 1797548432926179328 |
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| author | Giuliana Giorgianni Valeria Nori Andrea Baschieri Laura Palombi Armando Carlone |
| author_facet | Giuliana Giorgianni Valeria Nori Andrea Baschieri Laura Palombi Armando Carlone |
| author_sort | Giuliana Giorgianni |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T14:59:18Z |
| format | Article |
| id | doaj.art-e19553b03ab8453eaf8f1219bba5533c |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T14:59:18Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-e19553b03ab8453eaf8f1219bba5533c2023-11-20T20:21:17ZengMDPI AGCatalysts2073-43442020-11-011011129610.3390/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, ItalyA 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 |
| 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 |
| title | 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_short | Organocatalyzed Michael Addition to Nitroalkenes via Masked Acetaldehyde |
| title_sort | organocatalyzed michael addition to nitroalkenes via masked acetaldehyde |
| 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 |