Unsymmetrical Ferrocenylethylamine-Derived Monophosphoramidites:  Highly Efficient Chiral Ligands for Rh-Catalyzed Enantioselective Hydrogenation of Enamides and α-Dehydroamino Acid Derivatives

A new family of unsymmetrical ferrocenylethylamine-derived monophosphoramidites were synthesized and successfully applied in the Rh-catalyzed enantioselective hydrogenation of a range of enamides and α-dehydroamino acid esters, and ee values of up to 99.5% were obtained for both types of substrate....

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Veröffentlicht in:Journal of organic chemistry 2006-01, Vol.71 (1), p.393-396
Hauptverfasser: Zeng, Qing-Heng, Hu, Xiang-Ping, Duan, Zheng-Chao, Liang, Xin-Miao, Zheng, Zhuo
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Sprache:eng
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Zusammenfassung:A new family of unsymmetrical ferrocenylethylamine-derived monophosphoramidites were synthesized and successfully applied in the Rh-catalyzed enantioselective hydrogenation of a range of enamides and α-dehydroamino acid esters, and ee values of up to 99.5% were obtained for both types of substrate. These results suggest that unsymmetrical amine-derived monophosphoramidites can also exhibit excellent enantioselectivity for a broad range of substrates, comparable to or higher than those of the most efficient symmetrical amine-derived monophosphoramidites reported thus far.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051912s