Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile

Haitao Zhu, Pinhong Chen and Guosheng Liu*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: gliumail.sioc.ac.cn

H. Zhu, P. Chen, G. Liu, J. Am. Chem. Soc., 2014, 136, 1766-1769.

DOI: 10.1021/ja412023b

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Abstract

An oxidative cleavage of alkyl C-Pd bond by H₂O₂ enables a palladium-catalyzed intramolecular aminohydroxylation to give various heterocycles with good yields and excellent diastereoselectivities. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that a S_N2 type attack of water at a high-valent Pd center is involved.

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Key Words

oxazolidinones, hydrogen peroxide

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ID: J48-Y2014