4.7 Article

Unsymmetrical ferrocenylethylamine-derived monophosphoramidites:: Highly efficient chiral ligands for Rh-catalyzed enantioselective hydrogenation of enamides and α-dehydroamino acid derivatives

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 1, Pages 393-396

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo051912s

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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 alpha-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.

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