5267-67-4Relevant articles and documents
Ring opening of pymisyl-protected aziridines with organocuprates
Bornholdt, Jan,Felding, Jakob,Clausen, Rasmus P.,Kristensen, Jesper L.
supporting information; experimental part, p. 12474 - 12480 (2010/12/25)
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. Easy on'easy off: The pymisyl group is introduced as a new protecting group for the activation of aziridines towards ring opening with organocuprates (see scheme). It is readily removed under very mild conditions with thiolates. The versatility of the approach is illustrated in a new synthesis of Selegiline, a drug marketed for the treatment of Parkinson's disease.
EPC-synthesis of functionalised amides via chiral β-nitrogenated organolithium compounds
Foubelo, Francisco,Yus, Miguel
, p. 2911 - 2922 (2007/10/03)
The deprotonation of chiral chloroamides or carbamates 1, 4, 7, 10, 13 and 16 with n-butyllithium followed by in situ lithiation with lithium naphthalenide, both at -78°C in THF, leads to the formation of the corresponding chiral dianionic intermediates,
