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Stereoselective C(sp3)-C(sp2) Negishi coupling of (2-amido-1-phenylpropyl)zinc compounds through the steric control of β-amido group

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Abstract

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 β-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 β-NHCOC(CH3)2OTBS group specifically yielded anti 1-arylphenylethylamines.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000, China

    Shi Tang, ShuHua Li, Dong Zhou & HuiQiong Zeng

  2. Technical Institute of Physics and chemistry, Chinese Academy of Sciences, Beijing, 100080, China

    Shi Tang & NaiXing Wang

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  1. Shi Tang
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Correspondence to Shi Tang.

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Tang, S., Li, S., Zhou, D. et al. Stereoselective C(sp3)-C(sp2) Negishi coupling of (2-amido-1-phenylpropyl)zinc compounds through the steric control of β-amido group. Sci. China Chem. 56, 1293–1300 (2013). https://doi.org/10.1007/s11426-013-4880-2

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