Cobalt(diamine)-catalyzed cross-coupling reaction of alkyl halides with arylmagnesium reagents: stereoselective constructions of arylated asymmetric carbons and application to total synthesis of AH13205.
Cobalt(diamine)-catalyzed cross-coupling reaction of alkyl halides with arylmagnesium reagents: stereoselective constructions of arylated asymmetric carbons and application to total synthesis of AH13205.
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DOI：
10.1002/chin.200624061
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发表时间：
2006-01
影响因子：
15
通讯作者：
H. Ohmiya;H. Yorimitsu;K. Oshima
中科院分区：
文献类型：
--
作者：
H. Ohmiya;H. Yorimitsu;K. Oshima
一种钴二胺配合物催化伯、仲烷基卤化物与芳基格氏试剂的交叉偶联反应。证实了烷基卤化物对钴的氧化加成是通过自由基过程进行的。光学纯的Ueno-Stork晕缩醛经过非对映选择性交叉偶联反应，其产物转化为光学活性的THF衍生物。在钴催化下的顺序自由基环化/芳基化反应为合成前列腺素AH13205提供了极短的途径。
A cobalt-diamine complex catalyzes the cross-coupling reactions of primary and secondary alkyl halides with aryl Grignard reagents. It is confirmed that oxidative addition of alkyl halide to cobalt proceeds via a radical process. Optically pure Ueno-Stork halo acetals undergo diastereoselective cross-coupling reactions, the products of which are transformed into optically active THF derivatives. A sequential radical cyclization/arylation reaction under cobalt catalysis provides extremely short access to a synthetic prostaglandin AH13205.