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

Yingdong Luo; Guozhu Zhang; Erik S. Hwang; Thomas A. Wilcoxon; Liming Zhang

doi:10.3762/bjoc.7.69

Beilstein Journal of Organic Chemistry (May 2011)

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

Yingdong Luo,
Guozhu Zhang,
Erik S. Hwang,
Thomas A. Wilcoxon,
Liming Zhang

Affiliations

Yingdong Luo: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California, 93106, USA
Guozhu Zhang: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California, 93106, USA
Erik S. Hwang: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California, 93106, USA
Thomas A. Wilcoxon: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California, 93106, USA
Liming Zhang: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California, 93106, USA

DOI: https://doi.org/10.3762/bjoc.7.69
Journal volume & issue: Vol. 7, no. 1
pp. 596 – 600

Abstract

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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.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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