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Enantioselective Sulfa‐Michael Addition to α,β‐Unsaturated γ‐Oxoesters Catalyzed by a Metal‐Templated Chiral Brønsted Base
Author(s) -
Ding Xiaobing,
Lin Huihua,
Gong Lei,
Meggers Eric
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500033
Subject(s) - chemistry , enantioselective synthesis , catalysis , substituent , ligand (biochemistry) , imidazole , michael reaction , coordination sphere , organocatalysis , iridium , metal , organic chemistry , biochemistry , receptor
The enantioselective addition of aromatic thiols to α,β‐unsaturated γ‐oxoesters bearing an imidazole substituent in the δ position and catalyzed by an inert octahedral bis‐cyclometalated iridium(III) complex is reported. High enantioselectivity down to catalyst loadings of 0.05 mol % is achieved mediated by the formation of well‐arranged hydrogen bonds within the ligand sphere of the catalyst after the initial proton transfer. This work highlights the manifold opportunities provided by this metal‐templated design strategy in which the metal exerts a purely structural role whereas catalysis occurs through the organic ligand sphere (metal‐templated organocatalysis).