1029124-45-5Relevant academic research and scientific papers
Substrate Scope Evaluation of the Enantioselective Reduction of β-Alkyl-β-arylnitroalkenes by Old Yellow Enzymes 1-3 for Organic Synthesis Applications
Bertolotti, Mattia,Brenna, Elisabetta,Crotti, Michele,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Santangelo, Sara
, p. 577 - 583 (2016/02/23)
The substrate scope of the old yellow enzyme catalyzed reduction of β-alkyl-β-arylnitroalkenes is investigated. Compounds bearing either alkyl chains of increasing length at the carbon atom in position β to the nitro group or different substituents on the aromatic ring are prepared and submitted to bioreduction, to define the synthetic potential of this enantioselective reaction in the preparation of chiral fine chemicals. The versatility of the resulting nitroalkanes as chiral building blocks is shown by reducing the nitro group into a primary amine and by converting it into a carboxylic acid moiety by Meyer reaction. An "explosion" of chiral products can be observed by combining the highly enantioselective ene-reductase-mediated reduction of nitroalkenes with the chemical versatility of the nitro group.
A novel chiral bisphosphine-thiourea ligand for asymmetric hydrogenation of β,β-disubstituted nitroalkenes
Zhao, Qingyang,Li, Shengkun,Huang, Kexuan,Wang, Rui,Zhang, Xumu
supporting information, p. 4014 - 4017 (2013/09/02)
A novel chiral bisphosphine-thiourea ligand was developed and applied in the highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes (up to 99% yield and 99% ee). With low catalytic loading (0.25 mol %), 98% ee and 98% conversion were obta
Highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes
Li, Shengkun,Huang, Kexuan,Cao, Bonan,Zhang, Jiwen,Wu, Wenjun,Zhang, Xumu
, p. 8573 - 8576 (2012/09/10)
Building the building blocks: A highly enantioselective hydrogenation of ?-aryl-?-alkyl disubstituted nitroalkenes 1 has been developed. This method results in enantiomerically pure nitroalkanes 2, which are versatile precursors for chemical synthesis.
Highly enantioselective reduction of β,β-disubstituted aromatic nitroalkenes catalyzed by Clostridium sporogenes
Fryszkowska, Anna,Fisher, Karl,Gardiner, John M.,Stephens, Gill M.
, p. 4295 - 4298 (2008/12/20)
(Chemical Equation Presented) This is the first report of the use of Clostridium sporogenes extracts for enantioselective reduction of C=C double bonds of β,β-disubstituted (1) and α,β-disubstituted nitroalkenes (3). Crude enzyme preparations reduced aryl derivatives 1a-e and 1h, in 35-86% yield with ≥97% ee. Reduction of (E)- and (Z)-isomers of 1c gave the same enantiomer of 2c (≥99% ee). In contrast, α,β- disubstituted nitroalkene 3a was a poor substrate, yielding (S)-4a in low yield (10-20%), and the ee (30-70% ee) depended on NADH concentration. An efficient synthesis of a library of nitroalkenes 1 is described.
