A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.
Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride / V. Airoldi, O. Piccolo, G. RODA, R. APPIANI, F. BAVO, R. Tassini, S. Paganelli, S. ARNOLDI, M. PALLAVICINI, C. BOLCHI. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - 2020:2(2020 Jan 16), pp. 162-168.
|Titolo:||Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride|
PALLAVICINI, MARCO (Penultimo)
BOLCHI, CRISTIANO (Ultimo) (Corresponding)
|Parole Chiave:||Amination; Aquivion; Chemoselectivity; Cinacalcet; Sodium borohydride|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
Settore CHIM/08 - Chimica Farmaceutica
|Data di pubblicazione:||16-gen-2020|
|Data ahead of print / Data di stampa:||7-nov-2019|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/ejoc.201901614|
|Appare nelle tipologie:||01 - Articolo su periodico|
File in questo prodotto:
|efficient one-pot.pdf||Post-print, accepted manuscript ecc. (versione accettata dall'editore)||Embargo: 07/11/2020 Richiedi una copia|
|European_Journal_of_Organic_Chemistry reductive amination.pdf||Publisher's version/PDF||Administrator Richiedi una copia|