Gold-Catalyzed Highly Regioselective Oxidation of C-C Triple Bonds without Acid Additives: Propargyl Moieties as Masked α,β-Unsaturated Carbonyls

被引:177
作者
Lu, Biao [1 ]
Li, Chaoqun [1 ]
Zhang, Liming [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
基金
美国国家科学基金会;
关键词
ONE-POT SYNTHESIS; ALKYNES; KETONES; ACETYLENES; CYCLOPROPANATION; ORGANOSTANNANES; CYCLOADDITION; 1,2-DIKETONES; REARRANGEMENT; INTERMEDIATE;
D O I
10.1021/ja1072614
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylquinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile a,beta-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A range of functional groups such as THP, MOMO, N-3, OTBS, and N-Boc are tolerated. This reaction allows alpha,beta-unsaturated carbonyls to be masked as propargyl moieties, thus offering a practical solution to compatibility issues with these functional groups likely encountered in syntheses of complex structures.
引用
收藏
页码:14070 / 14072
页数:3
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