Alkenes oximes

In many of these cases, the nucleophile is a C=C double bond (usually an alkenic group and less frequently an aromatic group). Alkenic oxime mesylates enable intramolecular cyclization by an electrophihc addition of the double bond to the electrophilic intermediate. These reactions are terminated by a proton loss. 

The efficient activation of oxime sulfonates by organoaluminum reagents enables the intramolecular cyclization of alkenic oxime mesylates, which involves the electrophilic addition of the intermediate ni-trilium ion to the double bond. This results in the direct formation of a wide variety of structurally diverse carbocyclic and heterocyclic systems. Four distinct cyclization modes, i.e. endo(B)-endo, endo(B)-exo, exo(B)-endo and exo(B)-exo are possible, as shown in Scheme 4P The values in parentheses refer to the yields obtained using SnCU. 

The similar endo(B)-exo cyclizations have been effected with phosphorus pentoxide and more recently with trimethylsilyl polyphosphate (equation 32 and 33). The starting alkenic oximes are readily obtainable by the alkylation of the oxime dianion. Hence the overall process provides convenient access to the stereospecific synthesis of various heterocycles bearing substituents in the desired positions. 

Alkenes, Oximes, Imines, Amidines, Azo Compounds C=C, C=N, N=N Groups... 

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