Back to results
US 5,175,335 AGranted
Enantioselective hydrocyanation of aromatic vinyl compounds
AssigneeE. I. Du Pont de Nemours and Company
InventorsAlbert L. Casalnuovo, Thaliyil V. Rajanbabu, Lawrence W. Gosser, Ronald J. McKinney, William A. Nugent, Jr.
Life of this patent
Estimating the term…
Abstract
The invention provides a process for enantioselective hydrocyanation of aromatic vinyl compounds which produces nonracemic mixtures of chiral, arylpropionitriles; novel carbohydrate phosphorus and nickel catalyst compositions; and optically pure (S)-(-)-2-(6-metehoxy-2-naphthalene)propionitrile.
Claims12
A process for enantioselective hydrocyanation, comprising:
- reacting an aromatic vinyl compound of the formula
- Ar--CH.dbd.CH.sub.2
- wherein Ar is an aromatic or heteroaromatic radical;
- with a source of HCN;
- in the presence of a catalyst composition comprising zero-valent nickel and a chiral, nonracemic, bidentate organophosphorus ligand of the formula
- (R.sup.1).sub.2 --P--R.sup.2 --P--(R.sup.1).sub.2
- wherein each R.sup.1 is independently a C.sub.1 to C.sub.20 hydrocarbyl, alkoxy, or aryloxy, each optionally substituted with one or more alkyl, cycloalkyl, alkenyl, aralkyl, aryl, halogen, ether, ester, carboxy or amide groups;
- and R.sup.2 is a C.sub.4 to C.sub.40 carbohydrate, optionally substituted with one or more hydrocarbyl, halogen, ether, ester, alcohol, amide or ketone groups;
- to produce a nonracemic nitrile product of the formula ##STR26## wherein Ar is defined as above.
6 more elements
Dependencies are inferred from the claim text.