461383-57-3

Upstream product

• 1034147-27-7 1,1-dicarboxylic acid monomethyl ester-2-phenylcyclopropane 
• 3709-20-4 dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 19078-76-3 methyl 4-bromo-4-phenylbutanoate 
• 1821-12-1 4-Phenylbutyric acid 

Downstream Products

• 756419-35-9 methyl 4-amino-4-phenylbutanoate 
• 56553-09-4 (S)-(-)-5-phenylpyrrolidin-2-one 
• 461383-66-4 S-(2-iodophenethyl) 4-azido-4-phenylbutanethioate 
• 461383-59-5 4-azido-4-phenylbutanoyl chloride 
• 22050-10-8 (+/-)-5-phenyl-2-pyrrolidinone 
• 461383-58-4 4-azido-4-phenylbutanoic acid 

Relevant academic research and scientific papers

Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles

A general method for ring opening of various donor-acceptor cyclopropanes with the azide ion through an SN2-like reaction has been developed. This highly regioselective and stereospecific process proceeds through nucleophilic attack on the more-substituted C2 atom of a cyclopropane with complete inversion of configuration at this center. Results of DFT calculations support the SN2 mechanism and demonstrate good qualitative correlation between the relative experimental reactivity of cyclopropanes and the calculated energy barriers. The reaction provides a straightforward approach to a variety of polyfunctional azides in up to 91% yield. The high synthetic utility of these azides and the possibilities of their involvement in diversity-oriented synthesis were demonstrated by the developed multipath strategy of their transformations into five-, six-, and seven-membered N-heterocycles, as well as complex annulated compounds, including natural products and medicines such as (-)-nicotine and atorvastatin. A new world of opportunities: Stereospecific ring opening of donor-acceptor cyclopropanes with the azide ion gives rise to densely functionalized building blocks that are valuable for the assembly of a diverse range of N-heterocycles (see scheme; EDG=electron donating group; EWG=electron withdrawing group). These synthetic opportunities are provided by the simultaneous presence of the N3 group, which reacts as a latent amine or 1,3-dipole, easily modifiable donor and acceptor substituents, as well as the activated CH fragment.

Tandem ring-opening decarboxylation of cyclopropane hemimalonates with sodium azide: A short route to γ-aminobutyric acid esters

Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce γ-azidobutyric acids in good yields. These adducts were hydrogenated to form γ-aminobutyric acid (GABA) methyl esters.

Intramolecular Cyclization of Acyl Radicals onto the Azido Group: A New Radical Approach to Cyclized Lactams

(Equation Presented) Reagents: i, Bu3SnH/AlBN; ii, (TMS)3SiH/AlBN. Aryl- and alkyl-derived azidoacyl radicals, generated from thiolesters by intramolecular homolytic substitution at the sulfur, can undergo five- and six-membered cyclization onto the azido moiety to give cyclized lactams.