P-Stereogenic bisphosphines with a hydrazine backbone: from N-N atropoisomerism to double nitrogen inversion

The synthesis of P-stereogenic bisphosphine ligands starting from a phosphinous acid chiral synthon and hydrazine is reported. The dialkylation of the hydrazine backbone yielded atropo- and nitrogeninversion isomers which are in slow exchange. The crystallization of one of the isomers allowed us to...

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Detalhes bibliográficos
Autores: Prades, Amparo, Núñez-Pertíñez, Samuel, Riera i Escalé, Antoni, Verdaguer i Espaulella, Xavier
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2017
País:España
Recursos:Universidad de Barcelona
Repositório:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/110002
Acesso em linha:https://hdl.handle.net/2445/110002
Access Level:Acceso aberto
Palavra-chave:Lligands
Catàlisi asimètrica
Ligands
Enantioselective catalysis
Descrição
Resumo:The synthesis of P-stereogenic bisphosphine ligands starting from a phosphinous acid chiral synthon and hydrazine is reported. The dialkylation of the hydrazine backbone yielded atropo- and nitrogeninversion isomers which are in slow exchange. The crystallization of one of the isomers allowed us to study the reaction kinetics of the equilibria. The new ligands were tested in the Rh catalysed asymmetric hydrogenation of various benchmark substrates attaining up to 99% ee.