Highly Enantioselective Organocatalytic Michael Addition/Cyclization Cascade Reaction of Ylideneoxindoles with Isothiocyanato Oxindoles: A Formal [3+2] Cycloaddition Approach to Optically Active Bispirooxindole Derivatives. Issue 11 (8th February 2013)

• Record Type: Journal Article
• Authors: Tan, Fen; Cheng, Hong‐Gang; Feng, Bin; Zou, You‐Quan; Duan, Shu‐Wen; Chen, Jia‐Rong; Xiao, Wen‐Jing
• Is Part Of: European journal of organic chemistry. Issue 11(2013)
• Page Start: 2071
• Page End: 2075
• Publication Date: 2013-02-08
• Subjects: Asymmetric synthesis -- Organo­catalysis -- Michael addition -- Domino reactions -- Cascade reaction -- Cyclization -- Spiro compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300081
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A formal [3+2] cycloaddition involving the organocatalytic asymmetric Michael addition/cyclization cascade reaction of ylideneoxindoles with isothiocyanato oxindoles was developed. This method allows efficient and rapid synthesis of highly functionalized bispirooxindole products bearing three contiguous stereogenic centers with two quaternary stereocenters in almost quantitative yields with extremely high enantio‐ and diastereoselectivities. Abstract : A formal [3+2] cycloaddition involving the organocatalytic Michael addition/cyclization of ylideneoxindoles with isothiocyanato oxindoles was developed. This method allows efficient and rapid synthesis of highly functionalized bispirooxindoles bearing three contiguous stereogenic centers with two quaternary stereocenters in almost quantitative yields with extremely high enantio‐ and diastereoselectivities.