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

作者：Lu Biao; Li Chaoqun; Zhang Liming^*

来源：Journal of the American Chemical Society, 2010, 132(40): 14070-14072.

DOI：10.1021/ja1072614

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.

• 出版日期2010-10-13