1450890-99-9Relevant academic research and scientific papers
A General Strategy for the Stereoselective Synthesis of Pyrrole-Fused Chiral Skeletons: [3+2] Cycloaddition with 2-Nitro-2,3-Unsaturated Glycosides
Jiang, Nan,Mei, Yuling,Yang, Yu,Dong, Youxian,Ding, Zekun,Zhang, Jianbo
, p. 3973 - 3982 (2021)
In this study, a two-step methodology was developed for the synthesis of chiral pyrroles from 2-nitroglycals via Ferrier rearrangement and Barton-Zard reaction under mild conditions without transition metal catalysts. The Ferrier rearrangement reaction of 2-nitro-glycals and a series of O-nucleophiles proceeded smoothly in the presence of N-heterocyclic carbene (NHC) catalyst and K2CO3 which allowed the highly stereoselective synthesis of the diverse 2-nitro-2,3-unsaturated glycosides in excellent yields. Subsequently, the rearrangement products were conveniently transformed into the desired chiral pyrroles by [3+2] cycloaddition (Barton-Zard reaction) with isocyanoacetate in the presence of Cs2CO3. One-pot strategy was also successfully demonstrated for the gram-scale synthesis of one chiral pyrrole. This is the first report of stereoselective conversion from 2-nitroglycals to chiral pyrrole.
Synthesis of 2-nitroglycals from glycals using the tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine reagent system and base-catalyzed ferrier rearrangement of acetylated 2-nitroglycals
Dharuman, Suresh,Gupta, Preeti,Kancharla, Pavan K.,Vankar, Yashwant D.
, p. 8442 - 8450 (2013/09/24)
A reagent system comprising tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals. The base-catalyzed Ferrier rearrangement on tri-O-acetylated 2-nitroglycals has been reported for the first time. Reactivity of these nitroacetates and associated selectivity has been examined, and some of the products have been converted into 2,3-diamino-2,3-dideoxyglycosides and methyl N-acetyl-d-lividosaminide.
