863099-28-9Relevant academic research and scientific papers
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.
Addition reactions of iodomethyllithium to imines. A direct and efficient synthesis of aziridines and enantiopure amino aziridines
Concellon, Jose M.,Rodriguez-Solla, Humberto,Simal, Carmen
supporting information; experimental part, p. 4457 - 4460 (2009/05/07)
(Chemical Equation Presented) An efficient and general synthesis of aziridines by the reaction of imines derived from p-toluenesulfonamides with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, is reported for the first time. The reaction with the chiral aldimine derived from phenylalaninal allowed access to (2R,1′S)-2-(1′-aminoalkyl) aziridine with very high diastereoselectivity, in enantiopure form. A mechanism to explain this novel reaction is proposed.
Ring opening and expansion of aziridines in a silica-water reaction medium
Minakata, Satoshi,Hotta, Takahiro,Oderaotoshi, Yoji,Komatsu, Mitsuo
, p. 7471 - 7472 (2007/10/03)
Ring-opening reactions of N-tosylaziridines with water-soluble nucleophiles proceeded in a silica-water reaction medium. The system is applicable to a ring expansion of an aziridine with potassium thiocyanate, leading to a thiazolidine derivative.
Lewis base catalyzed ring opening of aziridines with silylated nucleophiles
Minakata, Satoshi,Okada, Yuriko,Oderaotoshi, Yoji,Komatsu, Mitsuo
, p. 3509 - 3512 (2007/10/03)
(Chemical Equation Presented) The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N′,N′- tetramethylethylenediamine, led to the production of β-functionalized sulfonamides in good to excellent yields with high regi
