A novel and highly stereoselective synthesis of Z-β-enaminonitriles from azides and α,β-unsaturated nitriles is reported. The reaction proceeds via a 1,3-dipolar cycloaddition-ring cleavage-rearrangement cascade mediated by a catalytic amount of Sc(OTf)3. A plausible reaction mechanism for this process is depicted.

A tin-catalyzed reaction of α-hydroxy ketones with 1,1-dicyanoalkenes produced 2-amino-4,5-dihydrofuran-3-nitriles. In the catalytic reaction, tin enolates were generated from α-hydroxy ketones as active catalytic species. The highly basic ability of the Sn-O bonds played an important role in the reactions. This tin-catalyzed reaction was highly atom-economical and required no other metal reage...

An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN(3) as a source of nitrogen in the presence of a catalytic amount of Cu(ClO(4))(2)·6H(2)O.

A simple, rapid and efficient practical method for one-pot synthesis of α-amino nitriles has been achieved by a threecomponent condensation of carbonyl compounds, amines and trimethylsilyl cyanide in the presence of p-toluenesulfonic acid (p-TsOH) as a catalyst at ambient temperature. Operational simplicity, economic consideration, high yield, short reaction time and low toxicity are the key fe...

To All(oc) involved: A palladium-catalyzed formal 5-endo-trig heteroannulation of enones generated in situ from amino acid derived β-keto nitriles has been realized (see scheme; Alloc=allyl carbamate). The reaction proceeds with allyl-group transfer from the carbamate protecting group to generate two new contiguous stereocenters, including one quaternary center, with high selectivity.