Synergistic Effect of the TiCl<sub>4</sub>/<i>p</i>-TsOH Promoter System on the Aza-Prins Cyclization
作者:Vianney Durel、Claudia Lalli、Thierry Roisnel、Pierre van de Weghe
DOI:10.1021/acs.joc.5b02342
日期:2016.2.5
A novel aza-Prins cyclization promoted by a synergistic combination between a Lewis acid and a Brønsted acid to efficiently afford piperidines is described. Contrary to what has been previously reported in the literature, the generality of the reaction employing N-alkyl, N-aryl, and nonprotected homoallylamines has been demonstrated. The reaction is highly diastereoselective depending on the homoallylic
描述了通过路易斯酸和布朗斯台德酸之间的协同组合促进有效地提供哌啶的氮杂-Prins环化。与先前文献中报道的相反,已经证明了使用N-烷基,N-芳基和未保护的高烯丙基胺的反应的一般性。该反应是高度非对映选择性的,这取决于所用的均烯丙基胺,优先导致反式非对映异构体的N -PMP均烯丙基胺和游离的均烯丙基胺,从而得到作为单个顺式非对映异构体的去保护的哌啶。