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Site-Specific Functionalization of 1,3-Dioxolane with Imines: A Radical Chain Approach to Masked α-Amino Aldehydes

Haipeng Zeng, Sen Yang, Haotian Li, Dengfu Lu*, Yuefa Gong* and Jin-Tao Zhu

*School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan, Hubei 430074, China, Email:,

H. Zeng, S. Yang, H. Li, D. Lu, Y. Gong, J.-T. Zhu, J. Org. Chem., 2018, 83, 5256-5266.

DOI: 10.1021/acs.joc.8b00715

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A thiol-promoted site-specific addition of 1,3-dioxolane to imines through a radical chain process enables a metal-free and redox-neutral conversion of inexpensive materials to a broad range of protected α-amino aldehydes in very good yields using only a catalytic amount of radical precursor. Both the thiol and a small amount of oxygen from air are indispensable to the success of this reaction.

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Key Words

protected carbonyl compounds, 1,3-dioxolanes, α-amino carbonyl compounds, multicomponent reactions

ID: J42-Y2018