Organocatalytic Tandem Reaction to Construct Six‐Membered Spirocyclic Oxindoles with Multiple Chiral Centres through a Formal [2+2+2] Annulation |
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| Authors: | Kun Jiang Zhi‐Jun Jia Shi Chen Li Wu Ying‐Chun Chen Prof. Dr. |
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| Affiliation: | 1. Key Laboratory of Drug‐Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China), Fax: (+86)?28‐85502609;2. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041 (China) |
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| Abstract: | 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). |
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| Keywords: | annulation asymmetric catalysis molecular complexity spiro compounds tandem reactions |
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