Table 1.

Scope of Oxidative O-Alkyl Hydroxamate Cyclization^a,^b

^aConditions: 1, PIFA (1.2 equiv), TFA (1.0/0.0 equiv), CH₂Cl₂ (0.15 M), 0 °C; then NH₃-MeOH, 20 min.

^bIsolated yields of oxamidations conducted with and w/o TFA, after purification by flash chromatography.

^cGenerated from E-1.

^dWorkup via hydrazinolysis.

^eGenerated from Z-1.

^fAn azocan-2-one, resulting from β-opening, was also isolated as a single diastereomer in 18/10% yield.

^gSee supporting information for the possible origins of rearrangement product 5.