Premium
Phase Transfer of Enantiopure Werner Cations into Organic Solvents: An Overlooked Family of Chiral Hydrogen Bond Donors for Enantioselective Catalysis
Author(s) -
Ganzmann Carola,
Gladysz John A.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800226
Subject(s) - enantiopure drug , enantioselective synthesis , diamine , ethylenediamine , aqueous solution , chemistry , hydrogen bond , catalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , molecule
Werner complexes go organic! When orange aqueous solutions of [Co(1,2‐diamine) 3 ]X 3 (X=I, Cl) are treated with solutions of NaBAr f in CH 2 Cl 2 (1:3 mol ratio), the aqueous phases decolorize (see scheme) and [Co(1,2‐diamine) 3 ](BAr f ) 3 ⋅ n H 2 O can be isolated from the CH 2 Cl 2 phases (78–89 %). The ethylenediamine complex can catalyze enantioselective Michael additions, presumably by an outer‐coordination‐sphere mechanism involving hydrogen bonding.