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Stereoselective Functionalization of 2‐(1‐Aminoalkyl)aziridines via Lithiation of Aziridine–Borane Complexes
Author(s) -
Concellón José M.,
Bernad Pablo L.,
Suárez José Ramón
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500113
Subject(s) - aziridine , electrophile , borane , enantiopure drug , stereoselectivity , chemistry , surface modification , combinatorial chemistry , organic chemistry , ring (chemistry) , enantioselective synthesis , catalysis
Highly selective functionalization of the aziridine ring of (2 S ,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.