Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines

An asymmetric hydrogenation of enamines is efficiently catalysed by rhodium complexed with a fluorinated version of the planar chiral paracyclophane-diphosphine ligand, Phanephos. This catalyst was shown to be very active, with examples operating at just 0.1 mol% of catalyst. This catalyst was then successfully adapted to Direct Asymmetric Reductive Amination, leading to the formation of several tertiary amines with moderate e.e., if activated ketone/amine partners are used.

Citation

Gilbert , S H , Tin , S , Fuentes , J A , Fanjul , T & Clarke , M L 2020 , ' Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines ' , Tetrahedron , vol. In Press , 131863 . https://doi.org/10.1016/j.tet.2020.131863

Publication

Tetrahedron

Status

Peer reviewed

DOI

https://doi.org/10.1016/j.tet.2020.131863

ISSN

0040-4020

Type

Journal article

Rights

Copyright © 2020 Elsevier Ltd. All rights reserved. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.tet.2020.131863

Description

We would like to thank the University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [Ph.D. studentship to SHG (PhD 2019); Grant code: EP/L016419/1], and Dr Reddys (EU Ltd.) for co-supporting a University studentship to ST (PhD 2017).