Asymmetric synthesis of functionalized 1,2,3,4-tetrahydroquinolines.
[reaction: see text] Highly enantioselective rhodium-catalyzed asymmetric hydrogenation (>98% ee) and Sharpless epoxidation (>90% ee) of o-nitrocinnamyl substrates lead to intermediates that can be transformed into tetrahydroquinoline derivatives. Starting materials are produced in high-yielding Heck reactions of an o-nitroaryl iodide and alpha-acetamidoacrylate or methyl acrylate.
Gallou-Dagommer
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Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
Gastaud
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RajanBabu
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D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry; D010575:Pesticides / Q000138:chemical synthesis / Q000737:chemistry; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D000975:Antioxidants; D010575:Pesticides; D017319:Photosensitizing Agents; D011804:Quinolines; C052355:2-methyl-1,2,3,4-tetrahydroquinoline