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Diastereoselective protonation on a radical anion in the photoallylation and photoreduction of 1,1-dicyano-2-methyl-3-phenyl-1-butene by allyltrimethylsilane

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Abstract

Diastereoselectivity in the photoallylation and photoreduction of 1,1-dicyano-2-methyl-3-phenyl-1-butene by allyltrimethylsilane in the presence of phenanthrene was dependent on the structures and stoichiometry of the added carboxylic acids. Diastereoselectivity increased up to 72% by the addition of equimolar amount of l-lactic acid based on the alkene.

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Notes

  1. In the presence of MeOH or H2O instead of AcOH as a proton source, the reaction proceeded slowly to give a complex mixture.

  2. The hydrogenation of compound 1 by Pd/C has been reported to proceed in a syn selective manner [19]. We prepared syn-rich mixtures of 3 and 4 by the hydrogenation of 1 by Pd/C and allylation of the syn-rich mixture of 4 by NaH and allyl bromide.

  3. The product ratio of allylation and reduction (3/4) listed in Table 1 are lower than the previous report using cyclohexylidenepropanedinitriles [10, 16]. The difference in the product ratio between previous and current studies may be due to the increased steric hindrance to protonation, and also due to the decrease of stoichiometry of carboxylic acids added in order to increase de.

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Acknowledgments

This work was partially supported by Grant-in-Aids for Scientific Research on Priority Areas “Reaction Control of Dynamic Complexes (420)” (16033252), “Advanced Molecular Transformations of Carbon Resources (444)” (18037063, 19020060), Scientific Research (B) (15350026), and Young Scientists (B) (16750039), and the Cooperation for Innovative Technology and Advanced Research in Evolutional Area (CITY AREA) program from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan.

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Authors and Affiliations

  1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan

    Hajime Maeda

  2. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Nana Nishitsuji & Kazuhiko Mizuno

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  1. Hajime Maeda
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  2. Nana Nishitsuji
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  3. Kazuhiko Mizuno
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Correspondence to Hajime Maeda.

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Maeda, H., Nishitsuji, N. & Mizuno, K. Diastereoselective protonation on a radical anion in the photoallylation and photoreduction of 1,1-dicyano-2-methyl-3-phenyl-1-butene by allyltrimethylsilane. Res Chem Intermed 36, 577–585 (2010). https://doi.org/10.1007/s11164-010-0165-y

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