Stereoselective C（sp^3）-C（sp^2） Negishi coupling of （2-amido-1-phenylpropyl）zinc compounds through the steric control of β-amido group

A controllable diastereoselective C（sp2）-C（sp3） Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides has been demonstrated for the first time, forming medicinally important 1-arylphenylethylamines. In the presence of Pd（OAc） 2 and S-phos, open-chain （2-amido-1-phenylethyl...

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Bibliographic Details
Published in:中国科学：化学英文版 2013 (9), p.1293-1300
Main Author: TANG Shi LI ShuHua ZHOU Dong ZENG HuiQion WANG NaiXin
Format: Article
Language:English
Subjects:
交叉偶联反应
空间位阻
立体选择性
耦合
苯基
酰氨基
锌化合物
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Summary:A controllable diastereoselective C（sp2）-C（sp3） Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides has been demonstrated for the first time, forming medicinally important 1-arylphenylethylamines. In the presence of Pd（OAc） 2 and S-phos, open-chain （2-amido-1-phenylethyl）zinc reagents bearing a -NHAc or NHCHO group underwent cross-coupling reaction to give syn 1-arylphenylethylamine as the major products, whereas the zinc reagents bearing a sterically hindered-NHCOC（CH3）2 OTBS group specifically yielded anti 1-arylphenylethylamines.
ISSN:1674-7291
1869-1870