Phospholane‐Phosphite Ligands for Rh Catalyzed Enantioselective Conjugate Addition: Unusually Reactive Catalysts for Challenging Couplings

The use of Rh catalysts derived from a phospholane‐phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required a...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2020-05, Vol.2020 (20), p.3071-3076
Main Authors: Gilbert, Sophie H., Fuentes, José A., Cordes, David B., Slawin, Alexandra M. Z., Clarke, Matthew L.
Format: Article
Language:English
Subjects:
Aromatic compounds
Aryl boronic acids
Asymmetric arylation
Asymmetric catalysis
Catalysts
Conjugates
Couplings
Enantiomers
Ligands
Michael addition
Phospholane ligands
Rhodium
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The use of Rh catalysts derived from a phospholane‐phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N‐CBz‐2‐3‐dehydro‐4‐piperidone, or the coupling of poorly reactive 2‐furyl boronic acids at ambient or near temperatures. Rh catalysts derived from the phospholane‐phosphite ligand, BOBPHOS (L1 in picture) promote transmetalation of aryl boronic acids more readily than a Rh/BINAP control systems. This leads to some difficult asymmetric arylations becoming feasible for the first time, or for others to operate using much lower excess of aryl boronic acid.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000336