Synthesis of Highly Enantioenriched C-Tertiary Amines From Boronic Esters: Application to the Synthesis of Igmesine
Synthesis of Highly Enantioenriched C-Tertiary Amines From Boronic Esters: Application to the Synthesis of Igmesine
复制标题
DOI：
10.1002/anie.201006037
复制
发表时间：
2011-01-01
影响因子：
16.6
通讯作者：
Aggarwal, Varinder K.
中科院分区：
文献类型：
--
作者：
Bagutski, Viktor;Elford, Tim G.;Aggarwal, Varinder K.
叔烷基胺是许多天然产品和药物中的常见基元，但以对映体富集型的形式获得它们有时会带来重大挑战。合成这些化合物的标准途径包括在酮胺中添加亲核试剂，例如有机金属试剂[1]或氰化物[2]，但也有其他间接方法的报道。[3]虽然许多方法在提供高水平的立体控制方面取得了成功，但选择性水平高度依赖于底物。
Tertiary alkylamines are common motifs in many natural products and pharmaceuticals but access to them in enantiomerically enriched form can sometimes present a major challenge. A standard route to these compounds involves the addition of nucleophiles, for example, organometallic reagents [1] or cyanide [2] to ketimines, but other indirect methods have also been reported.[3] Whilst many of these methods have been successful in delivering high levels of stereocontrol, the level of selectivity is highly substratedependent.