Organocatalytic Asymmetric Mannich Addition of 3-Fluorooxindoles to Dibenzo[ b, f][1,4]oxazepines: Highly Enantioselective Construction of Tetrasubstituted C-F Stereocenters

Bing Yu Li, Ye Lin, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

3-Fluorooxindoles and the dibenzo[b,f][1,4]oxazepane scaffolds are important pharmacophores that have important application in medicinal chemistry. An organocatalyzed asymmetric Mannich reaction of 3-fluorooxindoles with dibenzo[b,f][1,4]oxazepines affording various seven-member cyclic amines containing chiral tetrasubstituted C-F stereocenters was developed. These reactions which were catalyzed by a bifunctional Cinchona alkaloid-derived thiourea catalyst afforded a wide range of substrates in moderate to high yields with excellent diastereo- and enantioselectivities (up to 88% yield, >20:1 dr and >99% ee). A feasible reaction mechanism was also proposed.

Original languageEnglish
Pages (from-to)11752-11762
Number of pages11
JournalJournal of Organic Chemistry
Volume84
Issue number18
DOIs
Publication statusPublished - 20 Sept 2019

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Li, B. Y., Lin, Y., & Du, D. M. (2019). Organocatalytic Asymmetric Mannich Addition of 3-Fluorooxindoles to Dibenzo[ b, f][1,4]oxazepines: Highly Enantioselective Construction of Tetrasubstituted C-F Stereocenters. Journal of Organic Chemistry, 84(18), 11752-11762. https://doi.org/10.1021/acs.joc.9b01507