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New Chiral 1,2‐Diamines and Their Use in Zinc‐Catalyzed Asymmetric Hydrosilylation of Acetophenone
Author(s) -
Bette Virginie,
Mortreux André,
Ferioli Federico,
Martelli Gianluca,
Savoia Diego,
Carpentier JeanFrançois
Publication year - 2004
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.200400129
Subject(s) - hydrosilylation , diamine , acetophenone , chemistry , ethylene diamine , catalysis , ligand (biochemistry) , enantioselective synthesis , polymer chemistry , chiral ligand , organic chemistry , asymmetric induction , medicinal chemistry , nuclear chemistry , receptor , biochemistry
The preparation of two new series of chiral 1,2‐diamines and their use in the [ZnR 2 ‐diamine]‐catalyzed asymmetric hydrosilylation of acetophenone with poly(methylhydrosiloxane) (PMHS) in an aprotic medium is reported. The effect of structural modifications of the secondary diamine ligand, in particular a possible cooperative effect of two different types of chiral centers, on the N ‐benzylic side‐arms and on the ethylene bridge of the diamine skeleton, has been investigated. A new diamine ligand giving up to 91% ee is described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)