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Asymmetric synthesis of functionalized 1,2,3,4-tetrahydroquinolines
I Gallou-Dagommer1, P Gastaud, T V RajanBabu
1Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
Organic Letters
|June 22, 2001
Abstract:
[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.