Diastereoselective Construction of Densely Functionalized 1‐Halocyclopentenes Using an Alkynyl Halo‐Prins/Halo‐Nazarov Cyclization Strategy
作者:Georgios Alachouzos、Alison J. Frontier
DOI:10.1002/anie.201709482
日期:2017.11.20
developed. In the first step, a multicomponent alkynyl halo‐Prins reaction joins an enyne, a carbonyl derivative, and either a chloride, bromide, or iodide to produce a cyclic ether intermediate. In the subsequent step, the intermediate is ionized to generate a halopentadienyl cation, which undergoes an interrupted halo‐Nazarov cyclization. The products contain three new contiguous stereogenic centers
已经开发了一种非对映选择性的两步策略,用于合成具有多个手性中心的稠密官能化的1-卤代环戊烯。在第一步中,多组分炔基卤-普林斯反应将烯,羰基衍生物和氯化物,溴化物或碘化物连接起来,生成环状醚中间体。在随后的步骤中,中间体被离子化以生成卤代戊二烯基阳离子,该卤代戊二烯基阳离子经历了卤代-Nazarov环化的中断。该产品包含三个新的连续立体生成中心,它们通过高水平的立体控制生成,以及卤化乙烯,可以实现额外的功能化。该策略创建了两个新的碳-碳键,一个碳-卤键和一个碳-氧键。