1,4-Diazabicyclo[2.2.2]octane-Promoted Aminotrifluoromethylthiolation of α,β-Unsaturated Carbonyl Compounds: N-Trifluoromethylthio-4-nitrophthalimide Acts as Both the Nitrogen and SCF3 Sources

• Published in: Organic letters Vol. 17; no. 24; pp. 6090 - 6093
• Main Authors: Xiao, Qing, He, Qijie, Li, Juncheng, Wang, Jun
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.12.2015; Amer Chemical Soc
• Subjects: Amino Acids - chemical synthesis; Amino Acids - chemistry; Aza Compounds - chemistry; Catalysis; Chemistry; Chemistry, Organic; Cyclooctanes - chemistry; Mesylates - chemistry; Molecular Structure; Nitrogen - chemistry; Physical Sciences; Science & Technology; Stereoisomerism; BORONIC ACIDS; MEDIATED TRIFLUOROMETHYLTHIOLATION; IODONIUM YLIDE; AMINO; ENANTIOSELECTIVE CONJUGATE ADDITION; ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION; HYPERVALENT IODINE REAGENT; SUBSTITUENT CONSTANTS; COPPER-CATALYZED TRIFLUOROMETHYLTHIOLATION; STEREOSELECTIVE-SYNTHESIS
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/acs.orglett.5b03116

A novel difunctionalization reaction is described. It uses N-trifluoromethylthio-4-nitrophthalimide as the reagent, which serves as both the nitrogen and SCF3 sources. In the presence of DABCO (1,4-diazabicyclo[2.2.2]­octane), the nitrogen and SCF3 groups can be incorporated into α,β-unsaturated carbonyl compounds easily and give versatile β-amino ketones and esters in good yields. This difunctionalization reaction features mild reaction conditions, high atom-economy, and efficient access to α-SCF3 amino acids.