Ring opening of pymisyl-protected aziridines with organocuprates
Research output: Contribution to journal › Journal article › Research › peer-review
The pyrimidine-2-sulfonyl (pymisyl) group is introduced as a new protecting group that can be used to activate aziridines towards ring opening. It is readily introduced and removed under mild conditions. Regioselective ring opening of pymisyl-protected 2-methyl-aziridine with organocuprates gives the corresponding sulfonamides in high yields, and the pymisyl group can subsequently be removed upon treatment with a thiolate. The versatility of this new nitrogen protecting group is illustrated with a new synthesis of Selegiline, a monoamine oxidase-B inhibitor marketed for the treatment of Parkinson's disease.
|Journal||Chemistry: A European Journal|
|Publication status||Published - 2010|
Keywords: nitrogen heterocycles; protecting groups; ring opening; small ring systems; synthetic methods
- The Faculty of Pharmaceutical Sciences