Axially dissymmetric N-thioacylated (S)-(-)-1,1'-binaphthyl-2,2'-diamine ligands for copper-catalyzed asymmetric Michael addition of diethylzinc to alpha,beta-unsaturated ketone |
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| Authors: | Shi Min Duan Wei-Liang Rong Guo-Bin |
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| Affiliation: | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 453 Fenglin Lu, Shanghai 200032, China. Mshi@pub.sioc.ac.cn |
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| Abstract: | Axially chiral thioamide ligands L5, L6, L8, L11, and bis(thioamide) ligand L13 were prepared from the reaction of (S)-(-)-1,1'-binaphthyl-2,2'-diamine with acyl chlorides and phosphorus pentasulfide (P2S5). The catalytic asymmetric 1,4-addition of diethylzinc to alpha,beta-unsaturated ketones was examined using this novel chiral ligand system with 28-73% ee in moderate to good yields. |
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| Keywords: | (S)‐(–)‐1,1′‐binaphthyl‐2,2′‐diamine 2‐cyclohexen‐1‐one chalcone axially chiral amino‐thioamide ligand diethylzinc phosphorus pentasulfide (P2S5) |
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