Amido carbenoids

Amido carbenoids. Acetals of A-formyllactams (as well as imides and oxazolinones) engage in cyclopropanation with alkenes in the presence of Zn and CuCl. ... 

Prompted by our earlier work dealing with the internal dipolar cycloaddition reaction of mesoionic oxazolium ylides of type 74, we subsequently studied the rhodium(II) catalyzed reactions of the related a-diazo ketoamide system 154 <97JOC2001 04OL3241 05JOC2206>. Attack of the amido oxygen at the rhodium carbenoid produces a push-pull carbonyl ylide dipole (i.e., 155) that is isomeric with the isomiinchnone class of mesoionic betaines. 

Isomunchnone dipoles generated by the cyclization of rhodium carbenoid intermediates with adjacent amido groups have also been shown to undergo cycloaddition with both electron-rich and certain heteroaromatic 7i-bonds. For example, the catalytic decomposition of diazoimide 12 provided dipole 13 which subsequently added across the indole 7i-bond to give a cycloadduct possessing the aspidosperma alkaloid skeleton (Scheme 4) (95JOC6258). 

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