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Catalyst-controlled Wacker-type oxidation of homoallylic alcohols in the absence of protecting groups.

ABSTRACT: Homoallylic alcohols are oxidized to ?-hydroxy ketones using a TBHP-mediated Pd-catalyzed Wacker-type oxidation. The use of a bidentate ligand, quinoline-2-oxazoline (Quinox), and TBHP((aq)) as the terminal oxidant provides good yields of the desired products with reaction times significantly reduced as compared to the Tsuji-Wacker oxidation. Additionally, bis- and tris-homoallylic alcohols are oxidized to provide cyclic peroxyketals, presumably via nucleophilic attack of the methyl ketone product.

SUBMITTER: McCombs JR

PROVIDER: S-EPMC3092369 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Catalyst-controlled Wacker-type oxidation of homoallylic alcohols in the absence of protecting groups.

McCombs Jessica R JR Michel Brian W BW Sigman Matthew S MS

The Journal of organic chemistry 20110413 9

Homoallylic alcohols are oxidized to β-hydroxy ketones using a TBHP-mediated Pd-catalyzed Wacker-type oxidation. The use of a bidentate ligand, quinoline-2-oxazoline (Quinox), and TBHP((aq)) as the terminal oxidant provides good yields of the desired products with reaction times significantly reduced as compared to the Tsuji-Wacker oxidation. Additionally, bis- and tris-homoallylic alcohols are oxidized to provide cyclic peroxyketals, presumably via nucleophilic attack of the methyl ketone produ ...[more]

PMID: 21446720

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