N,N- and N,S-ligands for the enantioselective hydrosilylation of acetophenone with iridium catalysts

Enantiomerically pure C 2-symmetric diamines and dithioureas as well as a series of monothioureas have been tested as chiral inducers for hydrosilylation of acetophenone with iridium catalysts. Some new N,S-ligands have been synthesized in good yields, one of them bearing four chiral centers. Enanti...

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Bibliographic Details
Published in:Journal of molecular catalysis. A, Chemical Chemical, 2003-04, Vol.196 (1), p.137-143
Main Authors: Karamé, Iyad, Lorraine Tommasino, M, Lemaire, Marc
Format: Article
Language:English
Subjects:
Asymmetric catalysis
Chiral diamines
Chiral dithioureas
Iridium(I) catalysts
Ketone hydrosilylation
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Summary:Enantiomerically pure C 2-symmetric diamines and dithioureas as well as a series of monothioureas have been tested as chiral inducers for hydrosilylation of acetophenone with iridium catalysts. Some new N,S-ligands have been synthesized in good yields, one of them bearing four chiral centers. Enantioselectivities with dithioureas are better than the ones observed with analog diamine ligands. Up to 74% e.e. was reached for acetophenone hydrosilylation with a 10-fold excess of ligand versus iridium precursor.
ISSN:1381-1169
1873-314X
DOI:10.1016/S1381-1169(02)00643-X