Enantioselective Addition of Simple Hydrazines to Unsaturated Imides

Significance

This is the first example of enantio­selective conjugate addition of monosubstituted hydrazines to α,β-unsaturated imides. Although diastereoselective alternatives to this method (additions of hydrazines to chiral imides and additions of chiral hydrazines to achiral imides) are known, no enantioselective reaction has been reported so far. The attempts to establish a general and efficient protocol for addition of bisnucleophiles have been plagued with chemoselectivity issues. Here, using catalytic amounts of Lewis acid, products of great biological importance and chemical potential are obtained through a novel enantioselective and chemoselective reaction.