Stereoselective Synthesis of (Z)-beta-Enamido Triflates and Fluorosulfonates from N-Fluoroalkylated Triazoles

0507234 - ÚOCHB 2020 RIV DE eng J - Článek v odborném periodiku
Markos, Athanasios - Voltrová, Svatava - Motornov, V. - Tichý, David - Klepetářová, Blanka - Beier, Petr
Stereoselective Synthesis of (Z)-beta-Enamido Triflates and Fluorosulfonates from N-Fluoroalkylated Triazoles.
Chemistry - A European Journal. Roč. 25, č. 32 (2019), s. 7640-7644. ISSN 0947-6539. E-ISSN 1521-3765
Grant CEP: GA MŠMT LTAUSA18037
Institucionální podpora: RVO:61388963
Klíčová slova: 1,2,3-triazoles * enamides * triazolium salts * vinyl cations * vinyl triflates
Obor OECD: Organic chemistry
Impakt faktor: 4.857, rok: 2019
Způsob publikování: Omezený přístup
https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201901632

N-Fluoroalkylated 1,2,3-triazoles in the presence of triflic acid or fluorosulfonic acid underwent a cascade reaction consisting of triazole protonation, ring opening, nitrogen elimination, sulfonate addition, HF elimination, and hydrolysis to furnish novel trifluoromethanesulfonyloxy- or fluorosulfonyloxy-substituted enamides, respectively, in a highly stereoselective fashion. The vinyl triflates underwent cross-coupling reactions to a variety of substituted enamides and serve as sources of the aminovinyl cations. In reactions with triflic acid, electron-rich triazoles afforded 2-fluoroalkylated oxazoles.
Trvalý link: http://hdl.handle.net/11104/0298267