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Enantioselective and Z / E ‐Selective Conjugate Addition of α‐Substituted Cyanoacetates to Acetylenic Esters Catalyzed by Bifunctional Ruthenium and Iridium Complexes
Author(s) -
Hasegawa Yasuharu,
Gridnev Ilya D.,
Ikariya Takao
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003585
Subject(s) - iridium , bifunctional , enantioselective synthesis , ruthenium , chemistry , catalysis , enantiomer , conjugate , adduct , stereoselectivity , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , mathematics , mathematical analysis
Metal‐based catalysts : The title reaction provided the chiral adducts in high yields, excellent enantiomeric excess, and high Z / E selectivity. A combined NMR/DFT study revealed a key intermediate for the stereoselective reaction and a possible reaction mechanism (see the optimized transition‐state structure).