13906-90-6Relevant articles and documents
A general method for deprotection of N-toluenesulfonyl aziridines using sodium naphthalenide
Bergmeier, Stephen C.,Seth, Punit P.
, p. 6181 - 6184 (1999)
Deprotection of a variety of N-tosylaziridines with sodium naphthalenide provided the corresponding N-H-aziridines in excellent yield. No single electron transfer (SET) induced aziridine ring opening was seen under the conditions employed for the deprotection reaction.
Copper-catalyzed ring-opening reactions of alkyl aziridines with b2 pin2: Experimental and computational studies
Boldrini, Cosimo,Comparini, Lucrezia Margherita,Di Bussolo, Valeria,Di Pietro, Sebastiano,Favero, Lucilla,Menichetti, Andrea,Pineschi, Mauro
supporting information, (2021/12/17)
The possibility to form new C–B bonds with aziridines using diboron derivatives con-tinues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individua-tion of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2 pin2 ) in a regioselective nucleophilic addition reaction under copper catalysis.
Observations on the modified wenker synthesis of aziridines and the development of a biphasic system
Buckley, Benjamin R.,Patel, Anish P.,Wijayantha
, p. 1289 - 1292 (2013/04/10)
A cheap and reliable process for the modified Wenker cyclization to afford aziridines has been achieved using biphasic conditions for a range of amino alcohol starting materials. A 100 mmol "one-pot" process has also been devised, and the enantiopurity of the starting amino alcohol is retained in the aziridine product.
Addition reactions of chloro- Or iodomethyllithium to imines. Synthesis of enantiopure aziridines and β-chloroamines
Concellon, Jose M.,Rodriguez-Solla, Humberto,Bernad, Pablo L.,Simal, Carmen
supporting information; experimental part, p. 2452 - 2459 (2009/07/18)
We report a novel, simple, and efficient synthesis of aziridines and l-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodoor chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 °C. The reaction of in situ generated iodoor chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino- l-chloroalkanes with high stereoselectivity.
