21384-01-0Relevant academic research and scientific papers
Palladium-catalyzed cross-coupling of n -sulfonylaziridines with boronic acids
Duda, Megan L.,Michael, Forrest E.
supporting information, p. 18347 - 18349 (2014/01/06)
A mild palladium-catalyzed cross-coupling of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is presented. The reaction is highly regioselective and compatible with diverse functionality. A catalytic amount of base, a sterically demanding triarylphosphine ligand, and a phenol additive are critical to the success of the reaction. Coupling of a deuterium-labeled substrate established that ring opening of the aziridine occurs with inversion of stereochemistry.
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.
Process for the synthesis of gonadotropin releasing hormone antagonists
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, (2008/06/13)
The present invention relates to a process for preparing a compound of gonadotropin releasing hormone antagonists having a Formula I, in an efficient way, which involves preparation of key intermediates: 2-arylindole core; a chiral aziridine, in particular chiral nosyl aziridine; and an amine salt. The key process involves the coupling reaction of 2-arylindole and nosyl aziridine under boron trifluoride catalysis, which provides the final compound with unprecedented regioselectivity and enantioselectivity.
Nosylaziridines: Activated aziridine electrophiles
Maligres, Peter E.,See, Marjorie M.,Askin, David,Reider, Paul J.
, p. 5253 - 5256 (2007/10/03)
Nosylaziridines are highly reactive electrophiles towards a variety of nucleophiles yielding the corresponding SN2 adducts without competing attack on the nosyl functionality (SNAr). The resulting primary nosylamide adducts can he readily cleaved under mild conditions to provide the primary amines.
