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Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners.

ABSTRACT: This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)2, and iodosobenzene, (PhIO)n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.

SUBMITTER: Gunawan S

PROVIDER: S-EPMC8562708 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners.

Gunawan Steven S Bedard Nathan N Foley Christopher C Hulme Christopher C

Tetrahedron letters 20210317

This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)2, and iodosobenzene, (PhIO)n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol. ...[more]

PMID: 34737462

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