Enantioselective Vinylogous Organocascade Reactions

<p> Abstract</p> <p> Cascade reactions are powerful tools for rapidly assembling complex molecular architectures from readily available starting materials in a single synthetic operation. Their marriage with asymmetric organocatalysis has led to the development of novel techniques,...

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Detalhes bibliográficos
Autores: Hepburn, Hamish B., Dell’Amico, Luca, Melchiorre, Paolo
Formato: artículo
Fecha de publicación:2016
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/305754
Acesso em linha:http://hdl.handle.net/2072/305754
https://doi.org/10.1002/tcr.201600030
Access Level:acceso abierto
Palavra-chave:aminocatalysis
cascade catalysis
organocatalysi s
molecular complexity
vinylogous reactivity
Descrição
Resumo:<p> Abstract</p> <p> Cascade reactions are powerful tools for rapidly assembling complex molecular architectures from readily available starting materials in a single synthetic operation. Their marriage with asymmetric organocatalysis has led to the development of novel techniques, which are now recognized as reliable strategies for the one-pot enantioselective synthesis of stereochemically dense molecules. In recent years, even more complex synthetic challenges have been addressed by applying the principle of vinylogy to the realm of organocascade catalysis. The key to success of vinylogous organocascade reactions is the unique ability of the chiral organocatalyst to transfer reactivity to a distal position without losing control on the stereo-determining events. This approach has greatly expanded the synthetic horizons of the field by providing the possibility of forging multiple stereocenters in remote positions from the catalyst&rsquo;s point of action with high selectivity while simultaneously constructing multiple new bonds. This article critically describes the developments achieved in the field of enantioselective vinylogous organocascade reactions, charting the ideas, the conceptual advances, and the milestone reactions that have been essential for reaching highly practical levels of synthetic efficiency.</p>