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Expanding the Scope of Atropisomeric Monodentate P‐Donor Ligands in Asymmetric Catalysis: Hydrogen‐Transfer Reduction of α,β ‐Unsaturated Acid Derivatives by Rhodium/Ph‐binepine Catalysts
Author(s) -
Alberico Elisabetta,
Nieddu Ilenia,
Taras Rossana,
Gladiali Serafino
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690169
Subject(s) - chemistry , denticity , formic acid , rhodium , itaconic acid , transfer hydrogenation , ligand (biochemistry) , catalysis , hydroformylation , medicinal chemistry , hydrogen , combinatorial chemistry , organic chemistry , copolymer , ruthenium , metal , polymer , receptor , biochemistry
A range of α,β ‐unsaturated acids and esters have been selectively reduced to the corresponding saturated acid derivatives by hydrogen transfer. As the reducing agent, formic acid was used in the presence of Rh I complexes formed with the powerful chiral ligand Ph‐binepine ( 1 ), an axially chiral binaphthalene‐type monodentate P‐donor ligand. Very high stereoselectivities (up to 97% ee) were obtained in the case of itaconic acid ( 2a ).