Aziridine compounds, methods of preparation and reactions thereof
US5789599A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | May 6, 1994 |
| Grant date | Aug 4, 1998 |
| Priority date | — |
| Expiry date | May 6, 2014 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D203/24
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Novel N-sulfinyl-2-carboxyaziridine compounds and novel N-hydrogen-2-hydroxymethylaziridine compounds are provided. The asymmetric synthesis of N-sulfinylaziridines is readily accomplished in high diastereomeric purity and good yield by the Darzens-type reaction of the metal enolate of an .alpha.-haloester and an enantiopure sulfinimine. Ring-opening of these aziridines affords .alpha.-amino acids and the otherwise difficult to prepare syn-.beta.-hydroxy-.alpha.-amino acids, both key structural units found in many bioactive materials. The N-sulfinyl radical may be selectively removed from the novel aziridine compounds by treatment with acid or base. Alternatively, the N-sulfinyl radical may be oxidized to provide the corresponding N-sulfonyl-aziridine, or reduced to form the corresponding 1H-2-hydroxymethylaziridine, either of which may subsequently be ring-opened to provide precursors to bioactive compounds.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.