Tetrahedron Asymmetry p. 913 - 930 (1990)
Update date:2022-08-11
Topics:
Toth, Imre
Hanson, Brian E.
Davis, Mark E.
The results of the homogeneous asymmetric hydrogenation of several dehydroamino acids by rhodium-diene complexes of the chiral ligands; 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(bis(p-N,N-dimethylaminophenyl)phosphino)butane, 2a; 2,4-bis(bis(p-N,N-dimethylaminophenyl)phosphino)pentane, 3a; 2,3-bis(bis(p-N,N-dimethylaminophenyl)phosphino)butane, 4a; and their N-protonated and N-Me quaternized analogues are reported.The ligands comprise a versatile set which can be used both in organic and aqueous solvents.A detailed investigation of solvent and substituent effects isprovided.The presence of p-NMe2 groups enhances the rate of reaction in all cases.For the DIOP derivative, 2a, the presence of the dimethylamino group causes a reversal in the observed dominant product antipode.This is attributed predominantly to a change in preferred ligand conformation rather than to a kinetic difference between the two diastereomers of a single ligand conformation.
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