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

Beilstein Journal of Organic Chemistry

卷:7

Yingdong Luo¹  Guozhu Zhang¹  Erik S. Hwang¹  Thomas A. Wilcoxon¹  Liming Zhang¹ 

[1] Department of Chemistry and Biochemistry, University of California, Santa Barbara, California, 93106, USA;

关键词: allene;    catalysis;    gold;    oxidation;    regioselectivity;   

DOI  :  10.3762/bjoc.7.69

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown