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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.
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页码:14070 / 14072
页数:3
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