Ring opening of pymisyl-protected aziridines with organocuprates

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

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.
TidsskriftChemistry: A European Journal
Udgave nummer41
Sider (fra-til)12474-12480
StatusUdgivet - 2010

ID: 22728172