Ring opening of pymisyl-protected aziridines with organocuprates

Research output: Contribution to journalJournal articlepeer-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.
Original languageEnglish
JournalChemistry: A European Journal
Volume16
Issue number41
Pages (from-to)12474-12480
ISSN0947-6539
DOIs
Publication statusPublished - 2010

Bibliographical note

Keywords: nitrogen heterocycles; protecting groups; ring opening; small ring systems; synthetic methods

ID: 22728172