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Gold-catalyzed regioselective oxidation of terminal allenes: formation of ?-methanesulfonyloxy methyl ketones.

ABSTRACT: Synthetically useful ?-methanesulfonyloxy methyl ketones are readily prepared in one-step from terminal allenes in fair to good yields. The chemistry relies on a gold-catalyzed intermolecular oxidation of the 1,2-diene unit using 3,5-dichloropyridine N-oxide as the oxidant. The reaction tolerates a range of functional groups and shows excellent regioselectivity.

SUBMITTER: Luo Y 

PROVIDER: S-EPMC3107496 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones.

Luo Yingdong Y   Zhang Guozhu G   Hwang Erik S ES   Wilcoxon Thomas A TA   Zhang Liming L  

Beilstein journal of organic chemistry 20110511

Synthetically useful α-methanesulfonyloxy methyl ketones are readily prepared in one-step from terminal allenes in fair to good yields. The chemistry relies on a gold-catalyzed intermolecular oxidation of the 1,2-diene unit using 3,5-dichloropyridine N-oxide as the oxidant. The reaction tolerates a range of functional groups and shows excellent regioselectivity. ...[more]

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