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Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Allylation of Nitroalkanes with Monosubstituted Allylic Substrates

Xiao-Fei Yang, Wei-Hua Yu, Chang-Hua Ding, Qiu-Ping Ding, Shi-Li Wan, Xue-Long Hou*, Li-Xin Dai and Pin-Jie Wang

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email:

X.-F. Yang, W.-H. Yu, C.-H. Ding, Q.-P. Ding, S.-L. Wan, X.-L. Hou, L.-X. Dai, P.-J. Wang, J. Org. Chem., 2013, 78, 6503-6509.

DOI: 10.1021/jo400663d (free Supporting Information)


Pd-catalyzed asymmetric allylic alkylation of nitroalkanes and monosubstituted allylic substrates affords products with two adjacent chiral centers in excellent regio-, diastereo-, and enantioselectivities. Products can be transformed to optically active homoallylamines, 2,3-disubstituted tetrahydropyridines, and α,β-disubstituted amino acid derivatives.

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Key Words

Allylation, Nitro Compounds, Homoallylamines

ID: J42-Y2013