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21.10.1.1.2.3.1 Method 1: Direct Oxidation of Cyclic Amines by Ruthenium(IV) Oxide

DOI: 10.1055/sos-SD-021-00600

Smith, M. B.Science of Synthesis, (200521684.

Ruthenium(IV) oxide is an important reagent that oxidizes cyclic amines to lactams (Scheme 54), but the yield of the lactam depends on the substituent attached to the ring nitrogen and the size of the ring. For example, the oxidation of 1-(methylsulfonyl)piperidine (122, R1=SO2Me; n=3) with ruthenium(IV) oxide gives a 90% yield of the corresponding lactam 123 (R1=SO2Me; n=3).[‌154‌] The oxidation is successful for N-sulfonyl, N-formyl, N-acetyl, and N-trifluoroacetyl derivatives of pyrrolidine, piperidine, and azacycloheptane.[‌154‌]

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