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Ring Opening of Pymisyl‐Protected Aziridines with Organocuprates
Author(s) -
Bornholdt Jan,
Felding Jakob,
Clausen Rasmus P.,
Kristensen Jesper L.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001026
Subject(s) - aziridine , regioselectivity , ring (chemistry) , sulfonyl , chemistry , pyrimidine , protecting group , selegiline , monoamine oxidase , group (periodic table) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , enzyme , medicine , disease , parkinson's disease , alkyl , pathology
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.