Journal of Organic Chemistry p. 4422 - 4427 (1981)
Update date:2022-08-04
Topics:
Hobbs, Charles F.
Knowles, W. S.
The rhodium-catalyzed hydroformylation of vinyl acetate and related esters was carried out in the presence of chiral phosphine ligands of the DIOP type to give the corresponding optically active 2-(acyloxy)propanal, a precursor for the amino acid threonine.Ligand structure and the ligand/metal ratio were the primary factors controlling asymmetric induction; temperature, CO pressure, and solvent polarity had minor effects.The highest induction efficiencies, up to 51 percent ee, were obtained with the 5H-dibenzophospholyl derivative of DIOP (DIPHOL, 1e).
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