Synthesis and application of benzyl-TMS derivatives as bench stable benzyl anion equivalents
作者:Manas Das、Donal F. O'Shea
DOI:10.1016/j.tet.2013.05.078
日期:2013.8
derivatives are bench stable reagents yet can serve as benzyl anion equivalents under mild reaction conditions. Following activation with fluoride they can successfully participate in a wide range of additions to both non-enolizable and enolizable carbonyls. In addition, their use in the synthesis of isochromanones and trifluoromethylated amines is illustrated. The broad synthetic scope and mild practical
使用丁基锂/ KO甲苯的区域选择性金属化苄吨BU / TMP(H)(LINK金属化条件),并且随后转移金属化于Si通过与反应的TMSCl为取代benzyltrimethylsilanes的合成的一般单罐方法。ArCH 2 Si(Me)3衍生物是实验室稳定的试剂,但可以在温和的反应条件下用作苄基阴离子当量。用氟化物活化后,它们可以成功地参与不可烯醇化和可烯醇化羰基的多种加成。另外,还说明了它们在异色酮和三氟甲基化胺的合成中的用途。ArCH 2 Si(Me)3的广泛合成范围和温和的实际使用条件 试剂证明了其作为苄基阴离子当量的一般潜力。