Recyclable Organocatalyst for One‐Pot Asymmetric Synthesis of Dihydrofuranone and Tetrahydropyranone Spirooxindoles. Issue 1 (20th November 2018)

• Record Type: Journal Article
• Authors: Liu, Miao; Zhang, Xiaofeng; Huang, Xin; Dhawan, Gagan; Evans, Jason; Kaur, Manpreet; Jasinski, Jerry P.; Zhang, Wei
• Is Part Of: European journal of organic chemistry. Issue 1(2019)
• Page Start: 150
• Page End: 155
• Publication Date: 2018-11-20
• Subjects: Asymmetric synthesis -- Heterocycles -- One‐pot synthesis -- Organocatalyst -- Spirooxindoles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801480
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Recyclable fluorous bifunctional organocatalyst‐promoted one‐pot reactions of 1, 3‐dicarbonyl compounds, olefinic oxindoles, and formaldehyde through a Michael/aldol/cyclization sequence afford asymmetric dihydrofuranone and tetrahydropyranone spirooxindoles in 39–82 % yields with 3:1 to 6:1 dr and up to 99 % ee for the major diastereomers. Abstract : Recyclable fluorous bifunctional organocatalyst‐promoted one‐pot Michael/aldol/cyclization sequence affords asymmetric dihydrofuranone or tetrahydropyranone spirooxindoles in 39–82 % yields with 3:1 to 6:1 dr and up to 99 % ee for the major diastereomers