- Catalytic C-N and C-H Bond Activation: Ortho-Allylation of Benzoic Acids with Allyl Amines
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A facile insertion of ruthenium into aromatic C-H and allylic C-N bonds are the key steps in a [Ru(p-cymene)Cl2]2-catalyzed ortho-C-H allylation of benzoic acids. This protocol allows drawing on the large pool of allylic amines for state-of-the-art ortho-functionalizations of arenes, turning neutral amines into leaving groups. Concise syntheses of biologically active compounds provide further evidence of the synthetic potential of this methodology.
- Hu, Xiao-Qiang,Hu, Zhiyong,Zhang, Guodong,Sivendran, Nardana,Goo?en, Lukas J.
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supporting information
p. 4337 - 4340
(2018/07/29)
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- Efficient total synthesis of AI-77-B, a gastroprotective substance from Bacillus pumilus AI-77
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First total synthesis of AI-77-B (1), a gastroprotective substance from Bacillus pumilus AI-77, was achieved in a stereoselective and convergent manner. In this synthesis, the dihydroisocoumarin part 2 was constructed in one step through 1,2-addition of the benzylic anion 17b to Boc-L-leucinal 7b. The hydroxy amino acid 4 was elaborated from (R)-glutamic acid in a highly stereoselective manner. Condensation of 2·HCl and 4, intramolecular Pinner reaction, followed by mild hydrolysis afforded AI-77-B (1).
- Hamada,Hara,Kawai,Kohno,Shioiri
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p. 8635 - 8652
(2007/10/02)
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