Ring opening of pymisyl-protected aziridines with organocuprates

Research output: Contribution to journalJournal articlepeer-review

Standard

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 journalJournal articlepeer-review

Harvard

Bornholdt, J, Felding, J, Clausen, RP & Kristensen, JL 2010, 'Ring opening of pymisyl-protected aziridines with organocuprates', Chemistry: A European Journal, vol. 16, no. 41, pp. 12474-12480. https://doi.org/10.1002/chem.201001026

APA

Bornholdt, J., Felding, J., Clausen, R. P., & Kristensen, J. L. (2010). Ring opening of pymisyl-protected aziridines with organocuprates. Chemistry: A European Journal, 16(41), 12474-12480. https://doi.org/10.1002/chem.201001026

Vancouver

Bornholdt J, Felding J, Clausen RP, Kristensen JL. Ring opening of pymisyl-protected aziridines with organocuprates. Chemistry: A European Journal. 2010;16(41):12474-12480. https://doi.org/10.1002/chem.201001026

Author

Bornholdt, Jan ; Felding, Jakob ; Clausen, Rasmus Prætorius ; Kristensen, Jesper Langgaard. / Ring opening of pymisyl-protected aziridines with organocuprates. In: Chemistry: A European Journal. 2010 ; Vol. 16, No. 41. pp. 12474-12480.

Bibtex

@article{227b51f0e0f911dfb6d2000ea68e967b,
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.",
keywords = "Former Faculty of Pharmaceutical Sciences",
author = "Jan Bornholdt and Jakob Felding and Clausen, {Rasmus Pr{\ae}torius} and Kristensen, {Jesper Langgaard}",
note = "Keywords: nitrogen heterocycles; protecting groups; ring opening; small ring systems; synthetic methods",
year = "2010",
doi = "10.1002/chem.201001026",
language = "English",
volume = "16",
pages = "12474--12480",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "41",

}

RIS

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