The concept of preorganization involves engineering a receptor to be complementary to a guest prior to a binding event. This can render the host-guest interaction entropically and enthalpically more favorable. This notion can be extended further to chiral hydrogen bond donors as they are immensely popular in enantioselective organocatalysis.To put to test the effect of 'metal-driven preorganization in organocatalysis' we have chosen a 2-guanidinobenzimidazole derivative (GBI ) as a simple hydrogen bond donor. GBI  is an effective ligand, and upon complexation to transition or main group metals it becomes preorganized for several hydrogen bonding motifs as rotational degrees of freedom that are intrinsic to the ligand are greatly reduced. Upon preorganization both the reactivity and enantioselectivity are enhanced significantly.

Metal-driven preorganization in organocatalysis

245th National Meeting (2013)

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