Electronic and steric control in regioselective addition reactions of organolithium reagents with enaldimines |
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Authors: | Tomioka K Shioya Y Nagaoka Y Yamada K |
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Institution: | Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida Sakyo-ku, Kyoto 606-8501, Japan. tomioka@pharm.kyoto-u.ac.jp |
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Abstract: | A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic alpha,beta-unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nitrogen atom behaves as a 1,2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl or a bulky aryl group favors 1,4-addition of organolithium reagents. Electronic and steric tuning of a substituent on the imine nitrogen atom for a reaction mode was rationalized on the basis of molecular orbital calculations. |
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