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Org Biomol Chem. 2007 Oct 21;5(20):3340-6. Epub 2007 Sep 14.

Efficient asymmetric hydrogenation of olefins with hydrazine-derived diphosphoramidites.

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  • 1Laboratoire de Chimie Inorganique Mol√©culaire, Institut de Chimie, UMR 7177 CNRS and Universit√© Louis Pasteur, 1 rue Blaise Pascal, F-67008, Strasbourg, Cedex, France.


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 (t)BuHNNH(t)Bu resulted in ee's as high as 95%. The present results contradict previous reports on "short" diphosphoramidites.

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