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Enantioselective catalysis of carbonyl-ene and Friedel–Crafts reactions with trifluoropyruvate by ‘naked’ palladium(II) complexes with SEGPHOS ligands |
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| Authors: | Koichi Mikami Kohsuke Aikawa Satoshi Kainuma Yuji Kawakami Takao Saito Noboru Sayo Hidenori Kumobayashi |
| Institution: | aDepartment of Applied Chemistry, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan bFine and Aroma Chemical Institute, Takasago International Co., Hiratsuka-shi, Kanagawa 254-0073, Japan |
| Abstract: | Chiral dicationic SEGPHOS–Pd(II) complex gives high chemical yield, (E)-olefin selectivity, anti-diastereoselectivity, along with high enantioselectivity even with less reactive mono- and 1,2-disubstituted olefins in this much less reactive ketone-ene reactions. The high levels of enantioselectivity not only in carbonyl-ene but also in Friedel–Crafts reactions stem from the effective shielding with diphenyl groups on phosphines caused by the narrow dihedral angle of metal complexes with SEGPHOS. |
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