3017-54-7

Upstream product

• 3017-53-6 benzyl 2-bromopropionate 
• 100-51-6 benzyl alcohol 
• 17831-01-5 DL-alanine benzyl ester 

Downstream Products

• 910313-64-3 benzyl 5-oxo-2-nitro-2-methylpentanoate 
• 1390641-50-5 C₁₁H₁₃NO₅ 
• 53607-48-0 2-Bromo-2-nitro-propionic acid benzyl ester 

Relevant academic research and scientific papers

Enantioselective Addition of α-Nitroesters to Alkynes

By using Rh–H catalysis, we couple α-nitroesters and alkynes to prepare α-amino-acid precursors. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a RhIII–π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α-disubstituted α-amino esters.

Enantioselective synthesis of quaternary α-amino acids via l -tert-leucine-derived squaramide-catalyzed conjugate addition of α-nitrocarboxylates to enones

Enantioselective Michael addition of tertiary α-nitroesters to β-unsubstituted vinyl ketones has been carried out in the presence of an l-tert-leucine-derived squaramide as organocatalyst. The products, quaternary α-nitroesters, were formed in excellent yield and moderate to good ee's in most cases. Scale-up of the reaction and synthetic applications of the products, including transformation to representative quaternary α-amino acids, have also been demonstrated.

Inclusion complexes of EMPO derivatives with 2,6-di-O-methyl-β- cyclodextrin: Synthesis, NMR and EPR investigations for enhanced superoxide detection

The free radical trapping properties of eight 5-alkoxycarbonyl-5-methyl-1- pyrroline N-oxide (EMPO) type nitrones and those of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) were evaluated for trapping of superoxide anion radicals in the presence of 2,6-di-O-methyl-β-cyclodextrin (DM-β-CD). 1H-NMR titrations were performed to determine both stoichiometries and binding constants for the diamagnetic nitrone-DM-β-CD equilibria. EPR titrations were then performed and analyzed using a two-dimensional EPR simulation program affording 1: 1 and 1: 2 stoichiometries for the nitroxide spin adducts with DM-β-CD and the associated binding constants after spin trapping. The nitroxide spin adducts associate more strongly with DM-β-CD than the nitrones. The ability of the nitrones to trap superoxide, the enhancement of the EPR signal intensity and the supramolecular protection by DM-β-CD against sodium l-ascorbate reduction were evaluated. The Royal Society of Chemistry 2006.