Asymmetric synthesis of functionalized 1,2,3,4-tetrahydroquinolines.
نویسندگان
چکیده
[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.
منابع مشابه
pH-regulated asymmetric transfer hydrogenation of quinolines in water.
1,2,3,4-Tetrahydroquinolines exist as key structural elements in many natural products and have found broad commercial application. In particular, optically pure tetrahydroquinolines are commonly present in alkaloids and are required in pharmaceutical and agrochemical synthesis. Representative examples include the bioactive alkaloids (+)-galipinine and ( )-augustureine, and the antibacterial dr...
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A dual catalytic system consisting of indium triflate and a chiral imidazolidinone catalyzes the asymmetric addition of aldehydes to N-acyl quinoliniums furnishing optically active dihydroquinolines in good yields and excellent selectivities. The products were further functionalized into optically active tetrahydroquinolines, quinolines and 6-oxa-2-aza-bicyclo[3.3.1]nonanes.
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عنوان ژورنال:
- Organic letters
دوره 3 13 شماره
صفحات -
تاریخ انتشار 2001