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Supported Chiral Monodentate Ligands in Rhodium‐Catalysed Asymmetric Hydrogenation and Palladium‐Catalysed Asymmetric Allylic Alkylation
Author(s) -
Swennenhuis Bert H. G.,
Chen Ruifang,
van Leeuwen Piet W. N. M.,
de Vries Johannes G.,
Kamer Paul C. J.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900911
Subject(s) - chemistry , denticity , enantioselective synthesis , homoleptic , rhodium , tsuji–trost reaction , asymmetric hydrogenation , palladium , ligand (biochemistry) , alkylation , catalysis , allylic rearrangement , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , metal , biochemistry , receptor
A family of monodentate polystyrene‐supported phosphites, phosphoramidites and phosphanes has been prepared and evaluated as ligands in rhodium‐catalysed asymmetric hydrogenation and palladium‐catalysed asymmetric allylic alkylation. The supported ligands yielded active and enantioselective catalysts, which in selected cases match the performance of the nonsupported counterparts. As expected, the performance of the supported ligands in the rhodium‐catalysed hydrogenation depends on the nature of the ligand, the type of polymeric support, as well as on the substrate. Additionally, the supported ligands have been applied in the monodentate ligand combination approach, by combining them with nonsupported monodentate ligands. The partially supported heteroligand combinations possess different catalytic properties than the related nonsupported combinations. The heteroligand species, however, are not formed selectively, and nonsupported homoleptic complexes also contribute to the overall activity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)