494797-11-4

Usage

Uses

Used in Pharmaceutical Industry:
Butanoic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-, (2R)(9CI) is used as a chiral building block for the production of chiral drug molecules. Its unique structure allows for the creation of enantiomerically pure compounds, which are essential in the development of effective and safe medications.
Used in Agrochemical Industry:
In the agrochemical industry, Butanoic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-, (2R)(9CI) serves as a key intermediate in the synthesis of pesticides and herbicides. Its chiral properties enable the production of enantiomerically pure active ingredients, which can improve the efficacy and selectivity of these chemicals in controlling pests and weeds.
Used in Asymmetric Catalysis:
Butanoic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-, (2R)(9CI) is also important for its role in the development of amino acid-based chiral ligands for asymmetric catalysis. These ligands are crucial in facilitating enantioselective reactions, leading to the production of enantiomerically pure compounds with high yields and selectivity, which are vital in various chemical and pharmaceutical applications.

Upstream product

• 4749-37-5 3-nitroacrylic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 557-20-0 diethylzinc 
• 518352-05-1 (2S,3R)-3-(t-butyloxycarbonyl-aminomethyl)-pentan-1,2-diol 
• 780032-15-7 2-aminomethylbutyric acid methyl ester 
• 63819-91-0 methyl 2-ethyl-3-nitropropanoate 
• 518352-41-5 (2R)-N-t-butyloxycarbonyl-2-((4S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-enylamine 
• 518352-04-0 (2R)-2-((4S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-enylamine 
• 182682-27-5 (4S)-2,2-dimethyl-4-(1R)-1-nitromethyl-allyl-[1,3]dioxolane 

Relevant academic research and scientific papers

Conjugate Addition of Organozinc Compounds to Nitroolefins

Symmetrical (R2Zn) or mixed diorganozinc compounds (R 1ZnR2) smoothly react with a series of nitroolefins in the presence of catalytic amounts of copper(I) salts and provide synthetically versatile nitro compounds in moderate to good yields. Simple alkyl groups, functionalized residues, or mixed trimethylsilylmethyl organozinc compounds (TMSM)ZnR may be employed for conjugate addition, while the TMSM group is not being transferred. ipso-Substitution is observed in absence of the copper(I) salt. Enantiomerically pure copper(I) complexes with BINOL based chiral phosphoramidite ligands efficiently catalyze the addition of dialkylzinc compounds to nitroalkenes. For instance, diethylzinc addition occurs with high yields and excellent enantioselectivity. Nitrostyrene, 3-nitroacrolein dimethylacetal, and 3-nitroacrylates have been used as substrates. The nitroolefin moiety predominates over the acrylate moiety and acts as the more powerful Michael acceptor. 2-Alkyl-3-nitropropanoates are exclusively obtained with excellent yield and enantioselectivity. The products can easily be transformed into β2-homoamino acids, compounds of high relevance for different areas of preparative organic chemistry.

First synthesis of a beta(2)-homoamino acid by enantioselective catalysis.

The enantioselective conjugate addition of diethylzinc to the activated nitroolefin methyl 3-nitropropenoate is efficiently catalyzed by copper(I) complexes with BINOL-based enantiopure phosphoramidite ligands. The nitroolefin moiety acts as the predomina

Optically active nitroalkenes - Synthesis, addition reactions and transformation into amino acids

Optically active nitroalkenes 4 were synthesized via Henry reaction. Conjugate addition of vinylmagnesium bromide to 4 gave nitroalkane syn-5 while cyclopropanation with sulfur ylides or dibromocarbene afforded nitrocyclopropanes 8, 10 and 11 in a diaster