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[5]Ferrocenophanene–Phosphane Ligands for Enantioselective Rh‐Catalyzed Conjugate Additions
Author(s) -
Csizmadiová Jana,
Mečiarová Mária,
Rakovský Erik,
Horváth Branislav,
Šebesta Radovan
Publication year - 2011
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.201100908
Subject(s) - chemistry , enantioselective synthesis , cyclopentadienyl complex , rhodium , phenylboronic acid , stereoselectivity , conjugate , ligand (biochemistry) , enantiomer , catalysis , stereochemistry , medicinal chemistry , organic chemistry , mathematical analysis , mathematics , biochemistry , receptor
Ferrocenophanene–phosphane ligands with bridged cyclopentadienyl rings have been synthesized and characterized by spectroscopic methods. Rhodium complexes of these ligands can catalyze the Michael addition of phenylboronic acid to cyclic enones and lactones with good yields and an interesting level of stereoselectivity [up to a 95:5 enantiomeric ratio ( er )]. In comparison, a ligand without a bridge between the cyclopentadienyl rings affords a product with a lower enantioselectivity ( er = 78:22).