RESUMEN
We report for the first time that after O-acylation the conjugate addition products of (S)-N-(alpha-methylbenzyl)hydroxylamine undergo an efficient diastereoselective 3-exo-tet ring-closure reaction affording 2- and 2,3-disubstituted-N-alkylaziridines in good to excellent yields.
RESUMEN
We report the first racemic and stereoselective synthesis of cis- and trans-N-alkylaziridines viaN-chloroamines; using this methodology an N-3,4,5-trimethoxybenzylaziridine was synthesised and efficiently cleaved, affording the corresponding NH aziridine in high yield.
Asunto(s)
Aziridinas/química , Cloraminas/síntesis química , Catálisis , Ciclización , Estructura Molecular , Solventes , EstereoisomerismoRESUMEN
This paper describes a unique application of the fluoronium cation (F+) as an organocatalyst for mediating the reaction between N-substituted imines and ethyl diazoacetate affording excellent yields of N-substituted aziridines.
Asunto(s)
Aziridinas/síntesis química , Flúor/química , Compuestos Orgánicos/química , Sales (Química)/química , Acetatos/química , Aziridinas/química , Catálisis , Cationes/química , Iminas/química , Estereoisomerismo , Especificidad por SustratoRESUMEN
An efficient protocol for the synthesis of structurally diverse (diphenylphosphinoylmethyl)benzenes is described. The reaction employs readily available carboxylic acids, chlorodiphenylphosphine, and water as the reagents. A 97% reduction in the reaction times and substantially higher yields of products result, up to a 60% increase, if the reactions are performed under microwave irradiation. The first examples of transition-metal-catalyzed reactions applied to 4-bromo-1,3-bis(diphenylphosphinoylmethyl)benzene are also reported.