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Minimizing Aryloxy Elimination in Rh I ‐Catalyzed Asymmetric Hydrogenation of β‐Aryloxyacrylic Acids using a Mixed‐Ligand Strategy
Author(s) -
Li Yang,
Wang Zheng,
Ding Kuiling
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503229
Subject(s) - denticity , phosphine , chemistry , ligand (biochemistry) , catalysis , phosphine oxide , asymmetric hydrogenation , combinatorial chemistry , enantioselective synthesis , organic chemistry , medicinal chemistry , crystal structure , receptor , biochemistry
Abstract The first example of efficient asymmetric hydrogenation of challenging β‐aryloxyacrylic acids was realized using a Rh I ‐complex based on the heterocombination of a readily available chiral monodentate secondary phosphine oxide (SPO) and an achiral monodentate phosphine ligand as the catalyst. Excellent enantioselectivities (92–>99 % ee ) were achieved for a wide variety of chiral β‐aryloxypropionic acids with minor aryloxy elimination in most cases. The resultant products were readily transformed into biologically active compounds through simple synthetic manipulations.