Catalytic asymmetric benzylic C-H activation by means of carbenoid-induced C-H insertions |
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Authors: | Davies Huw M L Jin Qihui Ren Pingda Kovalevsky Andrey Yu |
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Institution: | Department of Chemistry, University at Buffalo, State University of New York, 14260-3000, USA. hdavies@acsu.buffalo.edu |
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Abstract: | TetrakisN-4-dodecylphenyl)sulfonyl]-(S)-prolinate]dirhodium Rh(2)(S-DOSP)(4)]-catalyzed decomposition of methyl aryldiazoacetates in the presence of substituted ethylbenzenes results in benzylic C-H activation by means of a rhodium-carbenoid-induced C-H insertion. A Hammet study showed that positive charge buildup occurred on the benzylic carbon in the transition state of the C-H activation step. C-H activation of toluene and isopropylbenzene is possible, but a competing double cyclopropanation occurs with these substrates. The C-H activation is highly regioselective and enantioselective, and in certain cases, moderate diastereoselectivity is also possible. |
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