ChemInform Abstract: Dimerization and Isomerization Reactions of α-Lithiated Terminal Aziridines

Autor:	Steven M. Miles, Christopher A. J. Brierley, Philip G. Humphreys, John G. Ward, David M. Hodgson
Rok vydání:	2008
Předmět:	chemistry.chemical_classification Deprotonation Terminal (electronics) Cyclopropanation Stereochemistry Chemistry Alkene chemistry.chemical_element Stereoselectivity Lithium General Medicine Isomerization
Zdroj:	ChemInform. 39
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200818094
Popis:	The scope of dimerization and isomerization reactions of α-lithiated terminal aziridines is detailed. Regio- and stereoselective deprotonation of simple terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide (LTMP) or lithium dicyclohexylamide (LiNCy2) generates trans-α-lithiated terminal aziridines. These latter species can then undergo dimerization or isomerization reactions depending on the nature of the N-protecting group. α-Lithiated terminal aziridines bearing N-alkoxycarbonyl (Boc) protection undergo N- to C-[1,2] migration to give N−H trans-aziridinylesters. In contrast, aziridines bearing N-organosulfonyl [tert-butylsulfonyl (Bus)] protection undergo rapid dimerization to give 2-ene-1,4-diamines or, if a pendant alkene is present, diastereoselective cyclopropanation to give 2-aminobicyclo[3.1.0]hexanes. All of these reactions were used as key steps in the preparation of synthetically and biologically important targets.
Databáze:	OpenAIRE
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