Organocatalytic Tandem Reaction to Construct Six-Membered Spirocyclic Oxindoles with Multiple Chiral Centres through a Formal [2+2+2] Annulation
Organocatalytic Tandem Reaction to Construct Six-Membered Spirocyclic Oxindoles with Multiple Chiral Centres through a Formal [2+2+2] Annulation
复制标题
通过形式[2 2 2]环化构建具有多个手性中心的六元螺环吲哚酮的有机催化串联反应
DOI：
10.1002/chem.200903009
复制
发表时间：
2010-01-01
影响因子：
4.3
通讯作者：
Chen, Ying-Chun
中科院分区：
文献类型：
--
作者：
Jiang, Kun;Jia, Zhi-Jun;Chen, Ying-Chun
通过[2+ 2+2]成环策略，成功地发展了一种高效的不对称合成六元螺环羟吲哚的串联反应.胺催化的立体选择性迈克尔加成的脂肪醛的缺电子的烯属羟吲哚基序得到手性C3组分，其进一步与不同的亲电试剂（活化的烯烃或亚胺）相结合，以提供螺环羟吲哚与通用的分子复杂性（高达6个连续的立体异构中心，高非对映体和对映体选择性）。
An efficient tandem reaction for the asymmetric synthesis of six-membered spirocyclic oxindoles has been successfully developed through a formal [2+ 2+2] annulation strategy. The amine-catalysed stereoselective Michael addition of aliphatic aldehydes to electron-deficient olefinic oxindole motifs gave chiral C3 components, which were further combined with diverse electrophiles (activated olefins or imines) to afford spirocyclic oxindoles with versatile molecular complexity (up to six contiguous stereogenic centres, high diastereo- and enantioselectivities).