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Organoiodine-Catalyzed Enantioselective Intermolecular Oxyamination of Alkenes

Chisato Wata and Takuya Hashimoto*

*Chiba Iodine Resource Innovation Center and Department of Chemistry, Graduate School of Science, Chiba University, 1-33, Yayoi, Inage, Chiba 263-8522, Japan, Email:

C. Wata, T. Hashimoto, J. Am. Chem. Soc., 2021, 143, 1745-1751.

DOI: 10.1021/jacs.0c11440

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Organoiodine(I/III) chemistry enables a metal-free, catalytic enantioselective intermolecular oxyamination of aryl- and alkyl-substituted alkenes with N-(fluorosulfonyl)carbamate as a bifunctional N,O-nucleophile with high enantioselectivity and electronically controlled regioselectivity. The oxyaminated products can be easily deprotected in one step to reveal free amino alcohols in high yields.

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Key Words

Oxazolidinones, Hypervalent Iodine Chemistry, Organocatalysis, Selectfluor

ID: J48-Y2021