Asymmetric synthesis of functionalized 1, 2, 3, 4-tetrahydroquinolines

I Gallou-Dagommer, P Gastaud, TV RajanBabu

Index: Gallou-Dagommer, Isabelle; Gastaud, Philippe; RajanBabu Organic Letters, 2001 , vol. 3, # 13 p. 2053 - 2056

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Citation Number: 42

Abstract

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 α-acetamidoacrylate or methyl acrylate.