Substrate‐Controlled Regioselectivity Switch in a Three‐Component 1, 3‐Dipolar Cycloaddition Reaction to Access 3, 3′‐Pyrrolidinyl‐Spirooxindoles Derivatives. Issue 12 (20th May 2022)

• Record Type: Journal Article
• Authors: Wang, Kai‐Kai; Li, Yan‐Li; Chen, Rong‐Xiang; Sun, Ai‐Li; Wang, Zhan‐Yong; Zhao, Ying‐Chao; Wang, Ming‐Yue; Sheng, Shi
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 12(2022)
• Page Start: 2047
• Page End: 2052
• Publication Date: 2022-05-20
• Subjects: 1, 3-dipolar cycloaddition -- spirooxindoles -- three-component reaction -- azomethine ylides -- switchable; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200269
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The additive‐free 1, 3‐dipolar cycloaddition reaction of isatin‐derived azomethine ylides with α‐cyano‐α, β‐unsaturated compounds was developed, which enabled diversity‐oriented synthesis of a series of novel and structurally complex 3, 3′‐pyrrolidinyl‐spirooxindoles derivatives containing four contiguous and two quaternary stereogenic centers in high yields (up to 92%) and excellent diastereoselectivities (up to >25:1 dr). The reaction displays switchable regioselectivity depending on the steric effect of the substrates. Abstract :