Azomethine imines, 1,3-dipolar functionality

The azomethine imines exhibit the typical cycloaddition behavior expected of 1,3-dipolar species [fSJ] Numerous [3+2] cycloaddition reactions have been performed [201 204] Tetracyanoethylene adds to azomethine imines across the nitnle function instead of the C=C double bond This reaction is a rare example of this type of periselectivity [208] (equation 47)... 

Dipolar cycloaddition reactions with stable and easily prepared azomethine imines, for the synthesis of a diverse array of heterocycles, have attracted considerable attention [125]. The complex RhjldS-MPPlM) (47) catalyzes the highly diastereoselective [3-l-2-l-l]-cycloaddition reaction between a diazo ketone and azomethine imines [126]. The final products are multi-functionalized bicyclic pyrazolidinone derivatives isolated in moderate to high yields (Scheme 9.12). 

To synthesize optically active nitrogen-containing chemicals with oxygen functionalities, it would be ideal to employ various types of unsaturated alcohols as a 1,3-dipolarophile. We developed a stoichiometric and a catalytic asymmetric 1,3-dipolar cycloaddition of azomethine imines 11 to a one-carbon homologated homoallylic alcohol 16A as shown in Table 11.5. 

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