Highly Enantioselective Michael Addition of 3-Aryloxindoles to Phenyl Vinyl Sulfone Catalyzed by Cinchona Alkaloid-Derived Bifunctional Amine-Thiourea Catalysts Bearing Sulfonamide as Multiple Hydrogen-Bonding Donors

• Published in: European Journal of Organic Chemistry Vol. 2011; no. 30; pp. 6078 - 6084
• Main Authors: Zhao, Mei-Xin, Tang, Wen-Hao, Chen, Ming-Xiao, Wei, Deng-Ke, Dai, Tong-Lei, Shi, Min
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.10.2011; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Enantio­selectivity; Exact sciences and technology; General and physical chemistry; Heterocycles; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Michael addition; Organic chemistry; Organocatalysis; Physical Sciences; Preparations and properties; Science & Technology; Synthetic meth­ods; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Michael addition; Heterocycles; ORGANOCATALYTIC ADDITION; Enantioselectivity; ASYMMETRIC CONJUGATE ADDITIONS; ALPHA,BETA-UNSATURATED IMIDES; ALDOL REACTIONS; N-FLUOROAMMONIUM SALTS; ALDEHYDES; BETA-KETO-ESTERS; FLUORINATION; Organocatalysis; 3-SUBSTITUTED OXINDOLES; MANNICH REACTIONS; Synthetic methods; Catalytic reaction; Sulfonamide; Quinuclidine derivatives; Sulfone; Nitrogen heterocycle; Organocatalyst; Bifunctional compound; Lactam; Quinoline derivatives; Thioureas; Alkaloid; Amine; Vinylic compound; Catalysis; Chemical synthesis; Hydrogen bond
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201100791

A highly enantioselective Michael addition of 3‐aryloxindole to phenyl vinyl sulfone catalyzed by a quinine‐derived bifunctional amine–thiourea‐bearing sulfonamide as multiple hydrogen‐bonding donor catalyst has been investigated. The corresponding adducts, which contain a chiral quaternary carbon center at the 3‐position of the oxindole, were obtained in moderate‐to‐good yields (52–86 %) with high‐to‐excellent enantioselectivities (83–98 % ee). We have developed a highly effective enantioselective Michael addition of 3‐aryloxindoles to phenyl vinyl sulfone catalyzed by a quinine‐derived bifunctionalamine–thiourea‐bearing sulfonamide as multiple hydrogen‐bonding donor catalyst, which provides the corresponding adducts in moderate‐to‐good yields (52–86 %) and with good‐to‐excellent enantioselectivities (83–98 %).