Epoxidation of a,P-unsaturated amides

Masakatsu Shibasaki of the University of Tokyo has developed effective procedures for the epoxidation of a,P-unsaturated amides with high . He has now reported (Angew. Chem. Int. Ed. 2004, 43y 317) reagents for the selective reduction of the epoxy amide 9 to either the p-hydroxy amide 10 or the a-hydroxy amide 11. 

A one-pot epoxidation/azide-opening sequence has been developed <05JA2147>. A samarium-BINOL-PhjAsO complex is used as a catalyst for enantioselective epoxidations of a,p-unsaturated amides. Upon addition of TMSN, a new samarium azide complex is generated which regioselectively opens the epoxide to form 120. This method has also been extended to thiols and cyanide. 

Table 13.34 Catalytic asymmetric epoxidation of a,p-unsaturated amides...

---