Synthesis 2012; 44(18): 2872-2884
DOI: 10.1055/s-0031-1290387
special topic
© Georg Thieme Verlag Stuttgart · New York

Unraveling the Synthetic Utility of the Regio- and Stereoselective Lithiation of Aziridines

Saverio Florio*
Consorzio Interuniversitario Nazionale sulle Metodologie e Processi Innovativi di Sintesi (CINMPIS), Università degli Studi di Bari ‘Aldo Moro’, Dipartimento Farmaco-Chimico, Via E. Orabona 4, 70125 Bari, Italy, Fax: +39(080)5442539   Email: florio@farmchim.uniba.it
› Author Affiliations
Further Information

Publication History

Received: 10 February 2012

Accepted after revision: 30 March 2012

Publication Date:
09 July 2012 (online)

Abstract

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.

 
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