Direct and enantioselective aldol reactions catalyzed by chiral nickel(II) complexes

A direct and asymmetric aldol reaction of N-acylthiazinanethiones with aromatic aldehydes catalyzed by chiralnickel(II) complexes is reported. The reaction gives thecorresponding O-TIPS-protected anti-aldol adducts in highyields and with remarkable stereocontrol and atom economy.Furthermore, the str...

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Detalhes bibliográficos
Autores: Kennington, Stuart C. D., Teloxa, Saul F., Mellado Hidalgo, Miguel, Galeote, Oriol, Puddu, Sabrina, Bellido, Marina, Romea, Pedro, Urpí Tubella, Fèlix, Aullón López, Gabriel, Font Bardia, Ma. Mercedes
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Recursos:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/178957
Acesso em linha:https://hdl.handle.net/2445/178957
Access Level:acceso abierto
Palavra-chave:Reacció aldòlica
Síntesi asimètrica
Níquel
Aldol reaction
Asymmetric synthesis
Nickel
Descrição
Resumo:A direct and asymmetric aldol reaction of N-acylthiazinanethiones with aromatic aldehydes catalyzed by chiralnickel(II) complexes is reported. The reaction gives thecorresponding O-TIPS-protected anti-aldol adducts in highyields and with remarkable stereocontrol and atom economy.Furthermore, the straightforward removal of the achiralscaffold provides enantiomerically pure intermediates ofsynthetic interest, which involve precursors for anti-a-amino-b-hydroxy anda,b-dihydroxy carboxylic derivatives. Theoret-ical calculations explain the observed high stereocontrol.