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

Citation
I. Gallou-dagommer et al., Asymmetric synthesis of functionalized 1,2,3,4-tetrahydroquinolines, ORG LETT, 3(13), 2001, pp. 2053-2056
Citations number
49
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
13
Year of publication
2001
Pages
2053 - 2056
Database
ISI
SICI code
1523-7060(20010628)3:13<2053:ASOF1>2.0.ZU;2-Q
Abstract
[GRAPHICS] Highly enantioselective rhodium-catalyzed asymmetric hydrogenation (> 98% e e) and Sharpless epoxidation (> 90% ee) of o-nitrocinnamyl substrates lead to intermediates that can be transformed into tetrahydroquinoline derivativ es, Starting materials are produced in high-yielding Heck reactions of an o -nitroaryl iodide and alpha -acetamidoacrylate or methyl acrylate.