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Preparation of New Ferrocenylmonophosphine Ligands Containing Two Planar Chiral Ferrocenyl Moieties and Their Use for Palladium‐Catalyzed Asymmetric Hydrosilylation of 1,3‐Dienes
Author(s) -
Han Jin Wook,
Tokunaga Norihito,
Hayashi Tamio
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200211)85:11<3848::aid-hlca3848>3.0.co;2-v
Subject(s) - trichlorosilane , chemistry , hydrosilylation , palladium , ferrocene , allylic rearrangement , diene , aryl , catalysis , silanes , medicinal chemistry , enantioselective synthesis , organic chemistry , alkyl , silane , silicon , electrochemistry , natural rubber , electrode
Bis{( R p )‐2‐[(1 S )‐1‐methoxyethyl]ferrocenyl}arylphosphines ( S , R p )‐ 9 (aryl=4‐MeOC 6 H 4 ( 9a ), Ph ( 9b ), 4‐CF 3 C 6 H 4 ( 9c ), 3,5‐(CF 3 ) 2 C 6 H 3 ( 9d )), which contain two planar chiral ferrocenyl moieties, were prepared via ( R p )‐1‐bromo‐2‐[(1 S )‐1‐methoxyethyl]ferrocene (( S , R p )‐ 8 ). Asymmetric hydrosilylation of linear 1,3‐dienes such as deca‐1,3‐diene ( 10a ) with trichlorosilane in the presence of a palladium catalyst coordinated with 9d gave allylic silanes of up to 93% ee.