750649-51-5Relevant articles and documents
Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut
?tv?s, Sándor B.,Kappe, C. Oliver,Llanes, Patricia,Pericàs, Miquel A.
, p. 8122 - 8126 (2020/11/03)
The two-step flow asymmetric synthesis of chiral γ-nitrobutyric acids as key intermediates of the GABA analogues baclofen, phenibut, and fluorophenibut is reported on a multigram scale. The telescoped process comprises an enantioselective Michael-type add
Catalytic asymmetric conjugate addition of nitroalkanes to 4-nitro5-styrylisoxazoles
Baschieri, Andrea,Bernardi, Luca,Ricci, Alfredo,Suresh, Surisetti,Adamo, Mauro F. A.
supporting information; experimental part, p. 9342 - 9345 (2010/03/24)
(Chemical equation presented) Nitro versus nitro: 4-Nitro-5- styrylisoxazoles were used as masked α,β-unsaturated carboxylic acids in the titled catalytic asymmetric transformation. The 4-nitroisoxazole core acts as an activator of the conjugated alkene and a latent carboxylate functionality. The reaction proceeded with 5 mol% of a readily prepared phasetransfer catalyst at room temperature with remarkable diastereo- and enantioselectivity (see scheme).
Highly enantioselective organocatalytic conjugate addition of nitromethane to α,β-unsaturated aldehydes: Three-step synthesis of optically active baclofen
Zu, Liansuo,Xie, Hexin,Li, Hao,Wang, Jian,Wang, Wei
, p. 2660 - 2664 (2008/09/19)
An efficient, organocatalytic, highly enantioselective, conjugate addition reaction of nitromethane with α,β-unsaturated aldehydes has been developed. The process serves as the key step for a practical 3-step synthesis of chiral baclofen, an antispastic drug.