NHC-catalyzed [4+2] cycloaddition reactions for the synthesis of 3′-spirocyclic oxindoles via a C–F bond cleavage protocol. Issue 13 (18th December 2017)

• Record Type: Journal Article
• Authors: Yan, Jun; Shi, Kuangxi; Zhao, Chengtao; Ding, Liyuan; Jiang, Shengsheng; Yang, Limin; Zhong, Guofu
• Is Part Of: Chemical communications. Volume 54:Issue 13(2018)
• Page Start: 1567
• Page End: 1570
• Publication Date: 2017-12-18
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc08048d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A chiral NHC-catalyzed cycloaddition of γ-fluoroenals is developed. The nucleophilic γ-carbon generated via C–F bond cleavage undergoes highly enantioselective cycloaddition (up to >99% ee) to isatins and provides 3′-spirocyclic oxindoles in good yields (up to 91%). Abstract : A chiral NHC-catalyzed cycloaddition of γ-fluoroenals is developed. The nucleophilic γ-carbon generated via C–F bond cleavage undergoes highly enantioselective cycloaddition (up to >99% ee) to isatins and provides 3′-spirocyclic oxindoles in good yields (up to 91%).