Novel Bis(1,3,2-diazaphospholidine) Ligands for Asymmetric Catalysis

A family of modularly designed chiral bis(1,3,2-diazaphospholidines) with N-aryl substituents (NP-PN) is reported. These compounds have been prepared in two steps from readily available (R,R)-1,2-diaminocyclohexane and tetrachlorodiphosphines. Examples in the set differ in the backbone and the aryl...

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Bibliographic Details
Published in:Organometallics 2013-05, Vol.32 (9), p.2497-2500
Main Authors: Arribas, Inmaculada, Álvarez, Eleuterio, Pizzano, Antonio
Format: Article
Language:English
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Summary:A family of modularly designed chiral bis(1,3,2-diazaphospholidines) with N-aryl substituents (NP-PN) is reported. These compounds have been prepared in two steps from readily available (R,R)-1,2-diaminocyclohexane and tetrachlorodiphosphines. Examples in the set differ in the backbone and the aryl substituents, aiming at their application in asymmetric catalysis. Thus, [Rh(NBD)(NP-PN)]BF4 complexes lead to active catalysts in the hydrogenation of methyl α-acetamidoacrylate, which provide enantioselectivities up to 96% ee. In addition, NP-PN ligands also generate active catalysts in the hydroformylation of vinyl acetate, leading to high regioselectivities (iso:n ratio higher than 99:1) and enantioselectivities up to 65% ee.
ISSN:0276-7333
1520-6041
DOI:10.1021/om400185q