Phase Transfer of Enantiopure Werner Cations into Organic Solvents: An Overlooked Family of Chiral Hydrogen Bond Donors for Enantioselective Catalysis | Zendy

Ganzmann Carola | Zendy; Gladysz John A. | Zendy

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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.

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