Lithiation of<i>N</i>-Alkyl-(<i>o</i>-tolyl)aziridine: Stereoselective Synthesis of Isochromans<sup>§</sup>
作者:Mariangela Dammacco、Leonardo Degennaro、Saverio Florio、Renzo Luisi、Biagia Musio、Angela Altomare
DOI:10.1021/jo9011943
日期:2009.8.21
investigated by using the aziridine ring capability to act as a directing metalation group. Trapped with electrophiles, the resulting o-aziridinyl benzyllithium 1-Li gives access to several functionalized aziridines 2a−j. The hydroxyalkylated derivatives 2d−j were converted into important scaffolds such as isochromans 3a−d. A stereoselective preparation of isochromans (R)-3b, (1R,3S)-3d, and (1R,3R)-3d has been
通过利用氮丙啶环作为直接金属化基团的能力,已经研究了邻甲苯基氮丙啶1的锂化反应。被亲电试剂截留后,生成的邻叠氮基苄基锂1-Li可与数个官能化的氮丙啶2a - j接触。羟烷基化衍生物2d - j被转化为重要的骨架,例如异色满3a - d。isochromans的立体选择性制备([R )- 3b中,(1 - [R,3小号)-3D,和(1R,3 R)-3d是从对映体富集的邻甲苯基拉啶开始开发的。