Chiba Iodine Resource Innovation Center and Department of Chemistry, Graduate School of Science, Chiba University, 1-33, Yayoi, Inage, Chiba 263-8522, Japan.
J Am Chem Soc. 2021 Feb 3;143(4):1745-1751. doi: 10.1021/jacs.0c11440. Epub 2021 Jan 22.
Metal-free, catalytic enantioselective intermolecular oxyamination of alkenes is realized by use of organoiodine(I/III) chemistry. The protocol is applicable toward aryl- and alkyl-substituted alkenes 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 without loss of enantioselectivity. A key to our success is the discovery of a virtually unexplored chemical entity, -(fluorosulfonyl)carbamate, as a bifunctional N,O-nucleophile.
通过有机碘（I/III）化学，实现了无金属、催化对映选择性的烯烃间氧胺化反应。该方案适用于具有高对映选择性和电子控制区域选择性的芳基和烷基取代的烯烃。氧胺化产物可以一步轻松脱保护，以高收率得到无对映选择性损失的游离氨基醇。我们成功的关键是发现了一种几乎未被探索的化学实体，即-(氟磺酰基)氨基甲酸酯，作为双功能的 N,O-亲核试剂。
