An intramolecular coupling approach to alkyl bioisosteres for the synthesis of multisubstituted bicycloalkyl boronates
作者:Yangyang Yang、Jet Tsien、Jonathan M. E. Hughes、Byron K. Peters、Rohan R. Merchant、Tian Qin
DOI:10.1038/s41557-021-00786-z
日期:2021.10
examined through the synthesis of a variety of other caged bicyclic molecules, ranging from [2.1.1] to [3.2.1] scaffolds. The modularity afforded by the pendant bridgehead boron pinacol esters generated during the cyclization reaction has been demonstrated through several downstream functionalizations, highlighting the ability of this approach to enable the programmed and divergent synthesis of multisubstituted
双环烃,尤其是双环[1.1.1]戊烷 (BCP),作为饱和生物电子等排物在制药、农用化学和材料化学中发挥着新兴作用。利用应变释放策略,先前的合成研究的特点是从 [1.1.1] 螺旋桨合成桥头取代的(C1,C3)BCP。在这里,我们描述了一种通过分子内环化获得多取代 BCP 的方法。除了 C1、C3-二取代 BCP 之外,该方法还能够从容易获得的环丁酮构建未充分探索的多取代(C1、C2 和 C3)BCP。通过合成各种其他笼状双环分子,范围从 [2.1.1] 到 [3.2.1] 支架,也检验了这种方法的广泛通用性。