Ring opening of pymisyl-protected aziridines with organocuprates

Jan Bornholdt; Jakob Felding; Rasmus Prætorius Clausen; Jesper Langgaard Kristensen

doi:10.1002/chem.201001026

Ring opening of pymisyl-protected aziridines with organocuprates

Jan Bornholdt, Jakob Felding, Rasmus Prætorius Clausen, Jesper Langgaard Kristensen

17 Citations (Scopus)

Abstract

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.

Original language	English
Journal	Chemistry: A European Journal
Volume	16
Issue number	41
Pages (from-to)	12474-12480
ISSN	0947-6539
DOIs	https://doi.org/10.1002/chem.201001026
Publication status	Published - 2 Nov 2010

Keywords

Former Faculty of Pharmaceutical Sciences

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10.1002/chem.201001026

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title = "Ring opening of pymisyl-protected aziridines with organocuprates",

abstract = "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.",

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author = "Jan Bornholdt and Jakob Felding and Clausen, {Rasmus Pr{\ae}torius} and Kristensen, {Jesper Langgaard}",

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year = "2010",

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doi = "10.1002/chem.201001026",

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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 - 2010/11/2

Y1 - 2010/11/2

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. 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.

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. 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.

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SN - 0947-6539

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EP - 12480

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

IS - 41

ER -

Ring opening of pymisyl-protected aziridines with organocuprates

Abstract

Keywords

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