31002-29-6

Upstream product

• 1517-69-7 (R)-1-phenylethanol 
• 492-37-5 hydratropic acid 
• 33122-25-7 tert-butyl 2-phenylpropaneperoxoate 
• 51250-91-0 bis(p-nitrophenyl) azidophosphonate 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 32366-25-9 1-azidoethylbenzene 
• 536-74-3 phenylacetylene 
• 209863-91-2 (S)-N,N-1,2-benzenedisulfonyl-1-phenylethylamine 

Downstream Products

• 2627-86-3 (S)-1-phenyl-ethylamine 

Relevant academic research and scientific papers

Direct Conversion of Activated Alcohols to Azides Using Diphenyl Phosphorazidate. A Practical Alternative to Mitsunobu Conditions

Fourteen alcohols were converted to their corresponding azides with inversion of configuration using diphenyl phosphorazidate and DBU.

Iron-Catalyzed Asymmetric Decarboxylative Azidation

The first iron-catalyzed asymmetric azidation of benzylic peresters has been reported with trimethylsilyl azide (TMSN3) as the azido source. Hydrocarbon radicals that lack of strong interactions were capable to be enantioselectively azidated. The reaction features good functional group tolerance, high yields, and mild conditions. The chiral benzylic azides can further be used in click reaction, phosphoramidation, and reductive amination, which demonstrate the synthetic values of this reaction.

Mesoionic carbene-boranes

Mesoionic carbenes (MICs), derived from alkylation and deprotonation of triazoles, are shown to form stable complexes with BH3. The synthesis of triazoles via Huigsen cycloadditions provides considerable structural diversity. Several routes to MIC-boranes are described, and their structures have been characterized by X-ray crystallography. As predicted on the basis of the increased σ-donor capacity of MICs by comparison to NHCs, the MIC-borane adducts are more reactive reducing agents.

A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm

A facile and efficient method for one-pot conversion of alcohols into azides using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of NaN3, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DMF affording the corresponding alkyl azides in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1° > 2° > 3°.

Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition

The use of chiral pybox ligands imparts enantioselectivity to the Cu I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of α-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis.

Process for the preparation of azide derivatives

A process for the preparation of azide derivatives useful as drugs, perfumes or intermediates of dyes by reacting an alcohol derivative with di-p-nitrophenyl phosphorazidate in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene.

N,N-1,2-benzenedisulfonylimide, a new cyclic leaving group for the stereoselective nucleophilic substitution of amines

We hereby report the preparation and nucleophilic substitutions of the N,N-1,2-benzenedisulfonylimide derivatives la and 2a of the chiral amines 1 and 2. The nucleophilic attack of KNO2 afforded the respective alcohols 3 and 4 with 84-90% inversion of configuration. Nucleophilic attack by the azide ion afforded the azide products 5 and 6 which were reduced to the corresponding inverted mines 1 and 2 (94-98.5% inversion). The improved leaving group ability of the N,N-1,2-benzenedisulfonylimides compared with previously reported N,N-disulfonylimides is discussed. Chiral GLC analysis of all products is summarized and the alternative chiral analysis of product 3 by 13C NMR using heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin as a chiral solvating agent (CSA) is discussed.

Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate

The direct stereoselective conversion of various alcohols and hexopyranoses into the corresponding alkyl azides and glycosyl azides, respectively, is efficiently accomplished by using bis(p-nitrophenyl) phosphorazidate and DBU.