Efficient asymmetric hydrogenation of olefins with hydrazine-derived diphosphoramidites

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...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 5; no. 20; pp. 3340 - 3346
Main Authors Eberhardt, Luc, Armspach, Dominique, Matt, Dominique, Oswald, Benoit, Toupet, Loic
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2007
Subjects
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Hydrazines - chemistry
Hydrogenation
Ligands
Naphthols - chemistry
Organophosphorus Compounds - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
TRANSITION
MONODENTATE PHOSPHORAMIDITE
CATALYZED HYDROGENATION
PHOSPHITES
PHOSPHORAMIDITE LIGANDS
COMPLEXES
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Summary: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 (BuHNNHBu)-Bu-t-Bu-t resulted in ee's as high as 95%. The present results contradict previous reports on "short" diphosphoramidites.
ISSN:1477-0520
1477-0539
DOI:10.1039/b710576b