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Synthesis of a New Class of Chiral 1,5‐Diphosphanylferrocene Ligands and Their Use in Enantioselective Hydrogenation
Author(s) -
Ireland Tania,
Tappe Katja,
Grossheimann Gabi,
Knochel Paul
Publication year - 2002
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 - 10.1002/1521-3765(20020215)8:4<843::aid-chem843>3.0.co;2-9
Subject(s) - enantioselective synthesis , substituent , moiety , ferrocene , chemistry , asymmetric hydrogenation , ligand (biochemistry) , stereochemistry , enantiomer , asymmetric induction , combinatorial chemistry , catalysis , organic chemistry , electrochemistry , receptor , biochemistry , electrode
Abstract A new family of ferrocenylphosphane ligands has been prepared. Their flexible synthesis allows many structural modifications. The asymmetric induction of these ligands was examined in the hydrogenation of functionalized C=C, C=O, and C=N bonds. The enantioselectivity of the reaction was strongly dependent on the substituent R at the position α to the ferrocene moiety. In many cases, both enantiomeric β ‐hydroxyesters of the reduction product can be obtained by simply replacing a dimethylamino group in the ligand with a methyl group.