作者:Melvin Raulin、Bruno Drouillat、Jérome Marrot、François Couty、Karen Wright
DOI:10.1016/j.tetlet.2022.153710
日期:2022.3
N-alkyl azetidines bearing a chiral substituent at the nitrogen atom, and a variable substituent at C-3 as a prochiral centre, react readily with cyanogen bromide even at low temperatures to produce the corresponding 3-bromo-N-cyanamides as diastereoisomeric mixtures via ring opening. This reaction was found to be diastereoselective (up to 80:20 dr). In one case, the major diastereomer could be isolated
N-烷基氮杂环丁烷在氮原子上带有一个手性取代基,在 C-3 上带有一个可变取代基作为前手性中心,即使在低温下也很容易与溴化氰反应生成相应的 3-溴-N-氰胺作为非对映异构体混合物。开环。发现该反应是非对映选择性的(高达 80:20博士)。在一种情况下,主要的非对映异构体可以通过重结晶分离,新产生的立体中心的构型由 X 射线晶体学确定。