Phosphine-Catalyzed Asymmetric Formal [4+2] Tandem Cyclization of Activated Dienes with Isatylidenemalononitriles: Enantioselective Synthesis of Multistereogenic Spirocyclic Oxindoles

• Published in: Advanced synthesis & catalysis Vol. 356; no. 4; pp. 736 - 742
• Main Authors: Hu, Fang-Le, Wei, Yin, Shi, Min
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 10.03.2014; WILEY‐VCH Verlag; Wiley
• Subjects: Activated; activated dienes; asymmetric [4+2] cyclization; Asymmetry; Catalysis; Catalysts; Chemistry; Chemistry, Applied; Chemistry, Organic; chiral phosphines; Dienes; multistereogenic spirocyclic oxindoles; organocascade reactions; Phosphines; Physical Sciences; Purity; Science & Technology; Synthesis; FACILE CREATION; ACID; chiral phosphines; asymmetric [4+2]cyclization; N-SULFONATED IMINES; BAYLIS-HILLMAN REACTION; multistereogenic spirocyclic oxindoles; FUNCTIONALIZED CYCLOPENTENES; activated dienes; SPIROOXINDOLES; organocascade reactions; 3+2 ANNULATION; CYCLOADDITION; ISATINS; CONSTRUCTION

The first highly enantioselective formal [4+2] tandem cyclizations between isatylidenemalononitriles and activated dienes catalyzed by bifunctional chiral phosphine catalysts have been developed, yielding multistereogenic spirocyclic oxindoles in high yields and excellent optical purity. This reacti...