Chiral phosphine-phosphite ligands in the highly enantioselective rhodium-catalyzed asymmetric hydrogenation

S Deerenberg; O Pàmies; M Diéguez; C Claver; P C Kamer; P W van Leeuwen

doi:10.1021/jo015705d

Chiral phosphine-phosphite ligands in the highly enantioselective rhodium-catalyzed asymmetric hydrogenation

J Org Chem. 2001 Nov 16;66(23):7626-31. doi: 10.1021/jo015705d.

Authors

S Deerenberg¹, O Pàmies, M Diéguez, C Claver, P C Kamer, P W van Leeuwen

Affiliation

¹ Institute of Molecular Chemistry, Universiteit van Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands.

PMID: 11701013
DOI: 10.1021/jo015705d

Abstract

We have investigated a series of enantiopure phosphine-phosphite ligands (P(1)-P(2) = ligands 1-4) in the rhodium-catalyzed asymmetric hydrogenation reaction. Intermediate [Rh(P(1)-P(2))(cod)]BF(4) and [Rh(P(1)-P(2))(5)]BF(4) complexes (cod = 1,5-cyclooctadiene; 5 = methyl acetamidoacrylate ester) were observed by (31)P[(1)H] NMR. The [Rh(P(1)-P(2))(cod)]BF(4) complexes were precursors to active catalysts of the asymmetric hydrogenation reaction of several prochiral dehydroamino acid derivatives under mild reaction conditions (1 bar of hydrogen and 20 degrees C). The enantiomeric excess reached up to 99%.