Radical-polar crossover domino reactions involving organozinc and mixed organocopper/organozinc reagents.

A domino process involving Michael addition and carbocyclization has been developed starting from beta-N-allylamino enoates and various organometallic reagents (organozinc halides, diorganozinc reagents, and copper/zinc mixed species). In all cases the mechanism of this domino reaction has been evidenced to involve a radical-polar crossover mechanism.

Synthesis of novel polycyclic indolyldiamines.

A rapid and stereoselective access to novel polycyclic indolyldiamines is described. The key step involves simple chemoselective transformations of a common bicyclic aminal intermediate, easily available on a large scale from an enantiomerically pure cyano oxazolopiperidine precursor.