TY - JOUR AU - Florio, Saverio TI - Unraveling the Synthetic Utility of the Regio- and Stereoselective Lithiation of Aziridines SN - 0039-7881 SN - 1437-210X PY - 2012 JO - Synthesis JF - Synthesis LA - EN VL - 44 IS - 18 SP - 2872 EP - 2884 ET - 2012/07/09 DA - 2012/09/06 KW - lithiation KW - heterocycles KW - electrophilic additions KW - stereo­selectivity KW - regioselectivity AB - The chemistry and synthetic utility of lithiated aziridines are discussed. Lithiated aziridines can be easily generated and captured by electrophiles, leading to more highly functionalized derivatives. Nitrogen dynamics and complexation phenomena play crucial roles in determining the regiochemistry of the lithiation process of aziridines and the stereochemistry of the reactions of the resulting lithiated species with electrophiles. Bench experiments combined with spectroscopic investigations and density-functional theory calculations are particularly useful in elucidating the chemistry of aziridines in their carbanionic form and in unraveling new aspects of the chemistry of aziridines. PB - © Georg Thieme Verlag DO - 10.1055/s-0031-1290387 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0031-1290387 ER -