Efficient enantioselective synthesis of CF2H-containing dispiro[benzo[b]thiophene-oxindole-pyrrolidine]s via organocatalytic cycloaddition. Issue 1 (1st December 2021)

• Record Type: Journal Article
• Authors: Deng, Yabo; Li, Yongzhen; Wang, Yalan; Sun, Shuo; Ma, Sichao; Jia, Pengfei; Li, Wenguang; Wang, Kairong; Yan, Wenjin
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 1(2022)
• Page Start: 210
• Page End: 215
• Publication Date: 2021-12-01
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01392k
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A novel kind of CF2 H-containing dispiro[benzo[ b ]thiophene-oxindole-pyrrolidine] has been achieved via an organocatalyzed 1, 3-dipole reaction. Abstract : An efficient and practical organocatalytic asymmetric [3 + 2] cycloaddition of difluoromethylated ketoimines and methyleneindolinones catalyzed by a quinine-derived squaramide has been disclosed. Under mild conditions, a broad range of CF2 H-containing dispiro[benzo[ b ]thiophene-oxindole-pyrrolidine]s bearing four adjacent chiral centers including two vicinal spiro quaternary stereocenters were obtained in high yields (up to 99% yield) with excellent diastereoselectivities (>20 : 1 dr, in all cases) and enantioselectivities (up to 99% ee).