Enantio- and Regioselective Intermolecular Benzylic and Allylic C[BOND]H Bond Amination

Authors

  • Yota Nishioka,

    1. Department of Chemistry, Faculty of Science, Graduate School, and International Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan)
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  • Dr. Tatsuya Uchida,

    1. Department of Chemistry, Faculty of Science, Graduate School, and International Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan)
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  • Prof. Tsutomu Katsuki

    Corresponding author
    1. Department of Chemistry, Faculty of Science, Graduate School, and International Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan)
    • Department of Chemistry, Faculty of Science, Graduate School, and International Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan)
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  • Financial support from Nissan Chemical Industries, Ltd., the World Premier International Research Center Initiative (WPI-I2CNER), the Global COE Programs, “Science for Future Molecular Systems”, and Grants-in-Aid for Scientific Research (23245009) from MEXT (Japan) is gratefully acknowledged. We are also grateful to Hideki Kobayashi and Kenji Suzuki, of Nissan Chemical Industries, Ltd. for DSC measurement of SESN3.

Abstract

original image

Smooth salen: Ru(CO)–salen complex 1 is an effective catalyst for asymmetric benzylic and allylic C[BOND]H bond amination using 2-(trimethylsilyl)ethanesulfonyl azide (SESN3) as the nitrene source. The reaction proceeded with high enantioselectivity and excellent regioselectivity. An ethyl group can be selectively aminated, even in the presence of an n-propyl group. No migration or isomerization of the double bond was observed.

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