Ring opening of pymisyl-protected aziridines with organocuprates
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Ring opening of pymisyl-protected aziridines with organocuprates. / Bornholdt, Jan; Felding, Jakob; Clausen, Rasmus Prætorius; Kristensen, Jesper Langgaard.
In: Chemistry: A European Journal, Vol. 16, No. 41, 2010, p. 12474-12480.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Ring opening of pymisyl-protected aziridines with organocuprates
AU - Bornholdt, Jan
AU - Felding, Jakob
AU - Clausen, Rasmus Prætorius
AU - Kristensen, Jesper Langgaard
N1 - Keywords: nitrogen heterocycles; protecting groups; ring opening; small ring systems; synthetic methods
PY - 2010
Y1 - 2010
N2 - 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.
AB - 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.
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.1002/chem.201001026
DO - 10.1002/chem.201001026
M3 - Journal article
C2 - 20839183
VL - 16
SP - 12474
EP - 12480
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 41
ER -
ID: 22728172