Enantioselective and Z/E-Selective Conjugate Addition of α-Substituted Cyanoacetates to Acetylenic Esters Catalyzed by Bifunctional Ruthenium and Iridium Complexes†
Yasuharu Hasegawa
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2637
Search for more papers by this authorProf. Dr. Ilya D. Gridnev
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2637
Search for more papers by this authorProf. Dr. Takao Ikariya
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2637
Search for more papers by this authorYasuharu Hasegawa
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2637
Search for more papers by this authorProf. Dr. Ilya D. Gridnev
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2637
Search for more papers by this authorProf. Dr. Takao Ikariya
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2637
Search for more papers by this authorThis work was financially supported by a Grant-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology (Japan, No. 18065007, 22225004) and by The G-COE Program.
Graphical Abstract
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).
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