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.