铑催化的三唑参与的分子内C-H键活化反应：立体专一性吡咯烷及其他相关环状化合物的制备
Rhodium-Catalyzed Intramolecular C-H Bond Activation with Triazoles: Preparation of Stereodefined Pyrrolidines and Other Related Cyclic Compounds.
作者信息
Senoo Masato, Furukawa Ayana, Hata Takeshi, Urabe Hirokazu
机构信息
Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa, 226-8501, Japan.
PRESTO, JST, Japan.
出版信息
Chemistry. 2016 Jan 18;22(3):890-5. doi: 10.1002/chem.201503823. Epub 2015 Dec 14.
On treatment of triazoles having an N-sulfonyl-protected benzylamine moiety with [Rh2 (C7 H15 CO2 )4 ], intramolecular C-H bond insertion takes place at the benzylic position to give cis-N-sulfonyl-2-aryl-3-[(sulfonylimino)methyl]pyrrolidines in good yields and with highly stereoselectivities. Analogously, the similar treatment of triazoles having an ether or even an alkyl moiety affords 2-alkyl- or 2-aryl-3-[(sulfonylimino)methyl]tetrahydrofurans or a 2-alkyl-3-[(sulfonylimino)methyl]cyclopentane in good yields.
用[Rh2 (C7 H15 CO2 )4 ]处理具有N-磺酰基保护的苄胺部分的三唑时，分子内C-H键在苄基位置发生插入反应，以良好的产率和高立体选择性得到顺式-N-磺酰基-2-芳基-3-[(磺酰基亚氨基)甲基]吡咯烷。类似地，对具有醚基甚至烷基部分的三唑进行类似处理，能以良好的产率得到2-烷基-或2-芳基-3-[(磺酰基亚氨基)甲基]四氢呋喃或2-烷基-3-[(磺酰基亚氨基)甲基]环戊烷。
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