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US 5,475,146 AGranted
Enantioselective hydroformylation
AssigneeE. I. Du Pont de Nemours and Company
InventorsTimothy A. Ayers, Thaliyil V. Rajanbabu
Life of this patent
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Abstract
Enantioselective hydroformylation of vinyl compounds using a catalyst composition of a chiral carbohydrate phosphorous ligand with a Rh, Pt, Co or Ir metal, to produce chiral 2-substituted propanals, wherein the phosphorous of the ligand is substituted with electron withdrawing groups.
Claims9
A process for enantioselective hydroformylation comprising:
- reacting a vinyl compound of formula I
- R--CH.dbd.CH.sub.2 I
- with a source of CO and H.sub.2, in the presence of a catalyst composition comprising one or more metals selected from the group consisting of Co, Rh, Ir, and Pt, and a chiral, nonracemic ligand of formula II
- (R.sup.1).sub.2 --P--O--R.sup.2 --O--P--(R.sup.1).sub.2 II
- to produce a nonracemic hydroformylated product of formula III ##STR14## wherein R is a C.sub.1 to C.sub.20 carboalkoxy, a C.sub.1 to C.sub.40 aromatic hydrocarbyl, or a C.sub.1 to C.sub.40 heterocyclic radical;
- each optionally substituted with one or more halo, alkoxy, carboalkoxy, hydroxy, amido or keto groups;
- each R.sup.1 is an electron-withdrawing group comprising an aromatic hydrocarbyl substituted with one or more halo, halogen-substituted alkyl groups, cyano, alkylsulfonyl, carboalkoxy, quaternary ammonium, nitro, amido or keto groups;
- or a heteroaromatic optionally substituted with one or more halo, halogen-substituted alkyl groups, cyano, alkyl sulfonyl, carboalkoxy, quaternary ammonium, nitro, amido or keto groups;
- R.sup.2 is a C.sub.4 to C.sub.40 dideoxy carbohydrate optionally substituted with one or more hydrocarbyl, halo, alkoxy, carboalkoxy, hydroxy, amido or keto groups.
6 more elements
Dependencies are inferred from the claim text.