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Issue 20, 2007
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Efficient asymmetric hydrogenation of olefins with hydrazine-derived diphosphoramidites

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Abstract

Enantiopure, BINOL-derived diphosphoramidites built upon an achiral hydrazine spacer are efficient ligands for the hydrogenation of 2-(acetylamino)-3-(aryl)-propenoic methyl esters. The activity and enantioselectivity of the hydrazine derivatives were shown to be markedly influenced by the nature of the two NR substituents, symmetrical but bulky R groups leading to the best results. A diphosphosphoramidite obtained from tBuHNNHtBu resulted in ee's as high as 95%. The present results contradict previous reports on “short” diphosphoramidites.

Graphical abstract: Efficient asymmetric hydrogenation of olefins with hydrazine-derived diphosphoramidites

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Supplementary files

Article information


Submitted
10 Jul 2007
Accepted
05 Sep 2007
First published
14 Sep 2007

Org. Biomol. Chem., 2007,5, 3340-3346
Article type
Paper

Efficient asymmetric hydrogenation of olefins with hydrazine-derived diphosphoramidites

L. Eberhardt, D. Armspach, D. Matt, B. Oswald and L. Toupet, Org. Biomol. Chem., 2007, 5, 3340
DOI: 10.1039/B710576B

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