133522-22-2

Upstream product

• 23190-16-1 (1R,2S)-2-Amino-1,2-diphenylethanol 
• 52340-78-0 (R,R)-hydroxybenzoin 
• 910916-39-1 (1R,2R)-1-diphenylphosphinoyloxy-2-hydroxy-1,2-diphenylethane 
• 910916-33-5 (1S,2R)-2-chloro-1,2-diphenyl-1-diphenylphosphinoyloxyethane 
• 68331-57-7 (1R,2R)-2-bromo-1,2-diphenylethanol 
• 1439-07-2 (R,R)-trans-stilbene epoxide 
• 181783-75-5 (+)-(R,R)-1,2-diphenylethylene carbonate 
• 183184-04-5 (R,R)-(+)-4,5-diphenyl-1,3,2-dioxathiolan-2-one 

Downstream Products

• 132486-62-5 (+)-(1S,2S)-1,2-diphenylethane-1,2-diazide 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 
• 224564-59-4 2-(diphenylphosphinoyl)-α-<(2S,3S)-2,3-diphenylaziridine-1-yl>toluene 
• 177977-65-0 ((1R,2S)-2-Azido-1,2-diphenyl-ethoxy)-tert-butyl-dimethyl-silane 
• 1605-06-7 (-)-(2S,3S)-2,3-diphenylaziridine 
• 23190-16-1 (1R,2S)-2-Amino-1,2-diphenylethanol 
• 178151-42-3 (1S,2R)-1,2-diphenyl-2-<(1,1-dimethylethyl)dimethylsiloxy>ethylamine 

Relevant academic research and scientific papers

Synthesis of Chiral Triazole-Based Halogen Bond Donors

The number of applications that use halogen bonding in the fields of self-assembly, supramolecular aggregation, and catalysis is growing. However, the accessibility of chiral halotriazoles shows that there is still a lot more to explore. The simple click-chemistry is applied for the straightforward synthesis of enantiomerically pure mono- and bidentate as well as multifunctional iodotriazole-based XB donors. The methodology is characterized by a wide variability due to easy access of chiral azides.

Diphenylphosphinoyl chloride as a chlorinating agent - The selective double activation of 1,2-diols

Treatment of 1,2-diols with diphenylphosphinoyl chloride in pyridine produces β-chloroethyl phosphinates which react with complete control of stereochemistry to give epoxides and azido-alcohols, useful intermediates in cyclopropane synthesis. The Royal Society of Chemistry 2006.

Single route to chiral syn- and anti-2-amino-1,2-diphenylethanols via a new stereodivergent opening of trans-1,2-diphenyloxirane

Oxiranyl ring opening of trans-stilbene oxide gave rise to anti- or syn-2-bromo-1,2-diphenylethanols, using either MgBr2·Et2O or MgBr2·Et2O, NaBr, and KBr with Amberlyst 15, respectively. Starting from optically pure (R,R)-trans-stilbene oxide, (1R,2R)- and (1R,2S)-2-amino-1,2-diphenylethanols were obtained in high yield and ee.

A practical route to enantiopure 1,2-aminoalcohols

A series of enantiopure aminoalcohols were synthesized from the corresponding diols by activation of the diols as cyclic carbonates, azide opening of the carbonates, and hydrogenation of the resulting azidoalcohols. Factors affecting the azide opening of the carbonates, a simple workup procedure, and a large scale synthesis of (1R,2S)-(-)-2-amino-1,2-diphenylethanol are described.

Asymmetric catalysis via chiral aziridines

The chiral bis(aziridines) 4, 6 and 7 have been synthesized and evaluated as chelating ligands for a variety of asymmetric transformations mediated by metals. The processes studied were the asymmetric addition of osmium tetroxide to olefins, copper-catalyzed asymmetric cyclopropanation and aziridination, palladium-catalyzed asymmetric allylic alkylation and asymmetric 1,2-addition of organolithium reagents to imines. In the best cases an enantiomeric excess >95% was obtained. Acta Chemica Scandinavica 1996.

Synthesis of Homochiral Amino Alcohols, Aziridines and Diamines via Homochiral Cyclic Sulphites

Vicinal diols react with thionyl chloride to give 1,2-cyclic sulphites in quantitative yield, which undergo facile ring opening by lithium azide in dimethylformamide to yield azido alcohols and the latter in turn have been stereoselectively transformed into amino alcohols, aziridines and diamines.