Efficient enantioselective synthesis of CF2H-containing dispiro[benzo[b]thiophene-oxindole-pyrrolidine]s via organocatalytic cycloaddition
Literature Information
Publication Date
2021-11-24
DOI
10.1039/D1QO01392K
Impact Factor
5.281
Authors
Yabo Deng, Yongzhen Li, Yalan Wang, Shuo Sun, Sichao Ma, Pengfei Jia, Wenguang Li, Kairong Wang, Wenjin Yan
View Original
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 CF2H-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).
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine
CAS Number:
485799-04-0
Molecular Formula:
C15H23BN2O3
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