Catalytic asymmetric cyanosilylation of ketones, aldehydes, thioketones, thioaldehydes, imines and hydrazones
US7078547B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Feb 5, 2003 |
| Grant date | Jul 18, 2006 |
| Priority date | — |
| Expiry date | Jan 10, 2024 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F7/188
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
One aspect of the present invention relates to a method for the catalytic asymmetric cyanosilylation of ketones, aldehydes, thioketones, thioaldehydes, imines and hydrazones. The critical elements of the method are: a non-racemic chiral tertiary-amine-containing catalyst; a substrate selected from the group consisting of ketones, aldehydes, thioketones, thioaldehydes, imines and hydrazones; and a silyl cyanide, e.g., trimethylsilyl cyanide. In preferred embodiments, the substrate is a ketone or aldehyde. A preferred embodiment of the present invention relates to practicing the method in a halocarbon solvent, e.g., chloroform. Another preferred embodiment of the present invention relates to practicing the method in an ester solvent, e.g., ethyl acetate. In certain embodiments, the methods of the present invention produce a silyl cyanohydrin with an enantiomeric excess greater than about 80%. In certain embodiments, the methods of the present invention produce a silyl cyanohydrin with an enantiomeric excess greater than about 90%.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.