Squaramide-Catalyzed Synthesis of Enantioenriched Spirocyclic Oxindoles via Ketimine Intermediates with Multiple Active Sites
Qiang-Sheng Sun
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Search for more papers by this authorHua Zhu
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Search for more papers by this authorYong-Jian Chen
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Search for more papers by this authorDr. Xiao-Di Yang
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Search for more papers by this authorCorresponding Author
Prof. Xing-Wen Sun
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)Search for more papers by this authorProf. Guo-Qiang Lin
Shanghai Institute of Organic Chemistry, CAS, 354 Fenglin Road, Shanghai, 200032 (China)
Search for more papers by this authorQiang-Sheng Sun
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Search for more papers by this authorHua Zhu
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Search for more papers by this authorYong-Jian Chen
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Search for more papers by this authorDr. Xiao-Di Yang
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Search for more papers by this authorCorresponding Author
Prof. Xing-Wen Sun
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China)Search for more papers by this authorProf. Guo-Qiang Lin
Shanghai Institute of Organic Chemistry, CAS, 354 Fenglin Road, Shanghai, 200032 (China)
Search for more papers by this authorGraphical Abstract
Five-membered spirocyclic oxindoles are generated in excellent yields (up to 94 %) and stereoselectivities (up to >20:1 d.r., >99 % ee) in a Michael–Mannich reaction of a ketimine intermediate that is catalyzed by a bifunctional quinine-derived squaramide. A scaled-up variant of this transformation also proceeded smoothly, highlighting the potential of this cascade process.
Abstract
A new method for the construction of five-membered spirocyclic oxindoles is based on a Michael–Mannich cascade reaction of a ketimine intermediated catalyzed by a bifunctional quinine-derived squaramide. The desired products were obtained in excellent yields (up to 94 %) and stereoselectivities (up to >20:1 d.r., >99 % ee). A scaled-up variant also proceeded smoothly showing that the one-pot reaction might find application in the synthesis of bioactive-compound libraries.
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