Stereoselective functionalization of 2-(1-aminoalkyl)aziridines via lithiation of aziridine-borane complexes.
Highly selective functionalization of the aziridine ring of (2S,1'S)-2-(1'-aminoalkyl)aziridines 1, through successive formation of aziridine-borane complexes, lithiation, treatment with a variety of electrophiles and final decomplexation is described. The influence of the structure of the starting complexes 2 and of the electrophiles in the stereoselectivity of this process has been studied. Finally, successive double lithiation-electrophile reactions were carried out affording enantiopure 1,2,3,3-tetrasubstituted aziridine-borane complexes with high selectivity.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain. jmcg@fq.uniovi.es
Bernad
Pablo L
PL
Suárez
José Ramón
JR
D001388:Aziridines / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D001388:Aziridines; D001880:Boranes; C033132:aziridine; D008094:Lithium