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Pd-Catalyzed enantioselective synthesis of 2-methyl-3-methyleneindoline |
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| Authors: | Chun-Hua Lu Sima Darvishi Vahid Khakyzadeh Changkun Li |
| Affiliation: | Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China; Department of Applied Chemistry, K. N. Toosi University of Technology, Tehran, Iran |
| Abstract: | A Pd-catalyzed enantioselective synthesis of 2-methyl-3-methyleneindoline in up to 89% yield and 84% ee from racemic vinyl benzoxazinanones has been developed with the help of (R,R)-BenzP* ligand. Mechanism studies support the formation of palladacyclobutane as the key intermediate via C2 attack to π-allyl Pd complex. The β-hydride elimination provides a new reaction pathway for the palladacyclobutane. |
| Keywords: | Palladium Asymmetric catalysis Vinyl benzoxazinanone 2-Methyl-3-methyleneindoline Palladacyclobutane |
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