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[3]Ferrocenophane Ligands with an Inserted Methylene Group
Author(s) -
Šebesta Radovan,
Bilčík Filip,
Horváth Branislav
Publication year - 2008
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.200800566
Subject(s) - chemistry , methylene , cyclopentadienyl complex , allylic rearrangement , ligand (biochemistry) , derivative (finance) , stereochemistry , planar chirality , catalysis , ring (chemistry) , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , enantioselective synthesis , receptor , biochemistry , financial economics , economics
New planar chiral [3]ferrocenophane aminosulfane and aminophosphane ligands displayed interesting results in model Pd‐catalyzed allylic substitution reactions. The phosphane derivative having a methylene group between the cyclopentadienyl ring and the phosphane group showed enantioselectivities up to 86 % ee , whereas the ligand without the methylene group afforded almost racemic allylation products. Analogous sulfane ligands showed the opposite trend. Tentative catalytic complexes were studied by 31 P NMR spectroscopy and DFT computational methods. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)