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Site-Specific Functionalization of 1,3-Dioxolane with Imines: A Radical Chain Approach to Masked α-Amino Aldehydes
- Zeng, Haipeng, Yang, Sen, Li, Haotian, Lu, Dengfu, Gong, Yuefa, Zhu, Jin-Tao
- Journal of organic chemistry 2018 v.83 no.9 pp. 5256-5266
- air, aldehydes, chemical reactions, chemical structure, imines, organic chemistry, oxygen, thiols
- A thiol-promoted site-specific addition of 1,3-dioxolane to imines through a radical chain process is described. This process represents a metal-free and redox-neutral way to convert inexpensive materials to a broad range of protected α-amino aldehydes in good to excellent yields using only a catalytic amount of radical precursor. Control experiments revealed that both the thiol and a small amount of oxygen from air are indispensable to the success of this reaction.