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Synthesis of Atropisomeric Hydrazides by One‐Pot Sequential Enantio‐ and Diastereoselective Catalysis

The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol. This strategy is based on a one‐pot sequence of two organocatalytic cycles featuring the enamine amination of branched aldehydes followed by nitrogen...

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Detalles Bibliográficos
Autores principales: Portolani, Chiara, Centonze, Giovanni, Luciani, Sara, Pellegrini, Andrea, Righi, Paolo, Mazzanti, Andrea, Ciogli, Alessia, Sorato, Andrea, Bencivenni, Giorgio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9826270/
https://www.ncbi.nlm.nih.gov/pubmed/36036383
http://dx.doi.org/10.1002/anie.202209895
Descripción
Sumario:The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol. This strategy is based on a one‐pot sequence of two organocatalytic cycles featuring the enamine amination of branched aldehydes followed by nitrogen alkylation under phase‐transfer conditions. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol. The permutation of organocatalysts allowed easy access to all stereoisomers, enabling a stereodivergent approach to enantioenriched atropisomeric hydrazides.