☆ 4.7 Article

Readily available chiral phosphine-aminophosphine ligands for highly efficient Rh-catalyzed asymmetric hydrogenation of α-enol ester phosphonates and α-enamido phosphonates

JOURNAL OF ORGANIC CHEMISTRY (2008)

Journal

JOURNAL OF ORGANIC CHEMISTRY

Volume 73, Issue 5, Pages 2011-2014

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/jo702488j

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Chemistry, Organic

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Abstract

[GRAPHICS] A new class of unsymmetrical hybrid phosphine-aminophosphine ligands has been prepared from commercially available, inexpensive (S)-1-phenylethylamine through a concise synthetic procedure. These ligands are not very sensitive to air and moisture, and displayed good enantioselectivities in the Rh-catalyzed asymmetric hydrogenation of various dimethyl alpha-benzoyloxyethenephosphonates bearing beta-aryl, beta-alkyl, and beta-alkoxy substituents and N-benzyloxycarbonyl alpha-enamido phosphonates, in which up to 97% ee was obtained. A side-by-side comparison study disclosed that these new phosphine-aminophosphine ligands showed better enantioselectivity than BoPhoz ligands.

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