Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands

A novel one-pot reductive methodol. for the synthesis of optically pure tert-butylmethylphosphine-borane is reported. The prepn. uses as the starting material tert-butylmethylphosphinous acid-borane, which is available in both enantiomeric forms from cis-1,2-aminoindanol and tert-butyldichlorophosph...

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Detalles Bibliográficos
Autores: Salomó i Prat, Ernest, Orgué Gassol, Sílvia, Riera i Escalé, Antoni, Verdaguer i Espaulella, Xavier
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/102067
Acceso en línea:https://hdl.handle.net/2445/102067
Access Level:acceso abierto
Palabra clave:Compostos fosforosos
Lligands (Bioquímica)
Phosphorus compounds
Ligands (Biochemistry)
Descripción
Sumario:A novel one-pot reductive methodol. for the synthesis of optically pure tert-butylmethylphosphine-borane is reported. The prepn. uses as the starting material tert-butylmethylphosphinous acid-borane, which is available in both enantiomeric forms from cis-1,2-aminoindanol and tert-butyldichlorophosphine. The process is based on the redn. of a mixed anhydride, the configurational stability of which has been studied in several solvents and temps. Tetrabutylammonium borohydride was the best reducing agent allowing for the development of a practical process. To demonstrate the utility of the new methodol., the product obtained in this manner was used in the prepn. of Quinox-P*.