Organocatalytic Tandem Reaction to Construct Six-Membered Spirocyclic Oxindoles with Multiple Chiral Centres through a Formal [2+2+2] Annulation

被引：224
|
作者：
Jiang, Kun [1 ]
Jia, Zhi-Jun [1 ]
Chen, Shi [1 ]
Wu, Li [1 ]
Chen, Ying-Chun [1 ,2 ]
机构：
[1] Sichuan Univ, W China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist,Dept Med Chem, Chengdu 610041, Peoples R China
[2] Sichuan Univ, W China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 09期
基金：
中国国家自然科学基金;
关键词：
annulation; asymmetric catalysis; molecular complexity; spiro compounds; tandem reactions; PUMMERER REACTION CHEMISTRY; ASYMMETRIC TOTAL-SYNTHESIS; STRUCTURE-BASED DESIGN; DIELS-ALDER REACTION; ENANTIOSELECTIVE FLUORINATION; CLAISEN REARRANGEMENT; RECEPTOR ANTAGONIST; VASOPRESSIN V-2; HIGHLY POTENT; SPIROTRYPROSTATIN;
D O I：
10.1002/chem.200903009
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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).
引用
收藏
页码：2852 / 2856
页数：5
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