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

✍ Scribed by Mei-Xin Zhao; Wen-Hao Tang; Ming-Xiao Chen; Deng-Ke Wei; Tong-Lei Dai; Min Shi

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 186 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100791

✦ Synopsis

Abstract

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).