73172-59-5

Upstream product

• 5623-21-2 α-allylbenzoin 
• 10133-06-9 methyl (+/-)-trans-(2,3)-epoxy butanoate 
• 591-51-5 phenyllithium 
• 75-07-0 acetaldehyde 
• 70-11-1 α-bromoacetophenone 
• 35660-91-4 (Z)-1-phenylbut-2-en-1-one 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 121788-93-0 3-Chlor-1-phenyl-2-(trimethylsiloxy)-1-butanon 

Downstream Products

• 121359-05-5 trans-5-methyl-3-phenyl-2-isoxazolin-4-ol 
• 34501-28-5 (+/-)-(RS)-((2SR,3SR)-3-methyloxiranyl)-phenylmethanol 
• 61752-45-2 Z-1-phenylpent-3-en-1-one 
• 74157-93-0 trans-1-phenyl-3-penten-1-one 
• 1210039-68-1 C₁₁H₁₂⁽²⁾H₂O₂ 
• 283166-69-8 3-hydroxy-2-(hydroxy-phenyl-methyl)-1-phenyl-butan-1-one 

Relevant academic research and scientific papers

Benchtop-Stabssle Hypervalent Bromine(III) Compounds: Versatile Strategy and Platform for Air- And Moisture-Stable λ3-Bromanes

We present the first synthesis of air/moisture-stable λ3-bromanes (9and10) by using a cyclic 1,2-benzbromoxol-3-one (BBX) strategy. X-ray crystallography and NMR and IR spectroscopy ofN-triflylimino-λ3-bromane (12) revealed that the bromine(III) center is effectively stabilized by intramolecular R-Br-O hypervalent bonding. This strategy enables the synthesis of a variety of air-, moisture-, and benchtop-stable Br-hydroxy, -acetoxy, -alkynyl, -aryl, and bis[(trifluoromethyl)sulfonyl]methylide λ3-bromane derivatives.

Convenient methods for the preparation of unsymmetrical double aldols

Double aldol reaction proceeded stereoselectively at one α-carbon of ketones to give α-(1-hydroxyalkyl)-β-hydroxyalkyl ketones (double aldols) in good to high yields by the following three methods: i) tin(II) trifluoromethanesulfonate-mediated aldol reaction of aldehydes with β-hydroxy ketones (mono-aldols) in the presence of tertiary amines, ii) samarium(II) iodide-mediated aldol reaction of aldehydes with alkyl or aryl oxiranyl ketones, iii) Sn(OTf)2- promoted aldol reaction of α-bromo ketones with aldehydes giving α-bromo-β-stannyloxy ketones which were then converted to titanium enolates on treatment with low-valent titanium. Double aldols were formed by subsequent reaction of the above titanium enolates with aldehydes in one-pot procedure. Further, small and medium-sized carbocyclic compounds whose ring skeletons were composed of double aldol structure were synthesized by SmI2-mediated intramolecular cyclization between oxiranyl ketone and aldehyde functions.

Unprecedented direct oxygen atom transfer from hypervalent oxido-λ3-iodanes to α,β-unsaturated carbonyl compounds: Synthesis of α,β-epoxy carbonyl compounds

Tetra-n-butylammonium oxido-λ3-iodane, prepared from 1-hydroxy-1,2-benziodoxol-3(1H)-one by reaction with tetra-n-butylammonium fluoride, directly undergoes oxygen atom transfer to γ,β-unsaturated carbonyl compounds, yielding epoxides.

Baker's Yeast-mediated Transformations of α-Keto Epoxides

αβ-Epoxy ketones on treatment with baker's yeast yield different types of products depending on their substitution.Small groups such as H or Me attached at the epoxy end protect that end from attack.Thus,1-acyl epoxides with H, methyl or propyl as the 2-e

Ttimethylsilyl Cyanide - A Reagent for Umpolung, XVIII. - Nucleophilic Acylation of α-Chlorocarbonyl Compounds - a Novel and Diastereoselective Approach to Substituted α,β-Epoxy Ketones

The addition products of trimethylsilyl cyanide and benzaldehyde (1a), furfural (1b), and α,β-unsaturated aldehydes 2a-c, respectively, react after deprotonation with α-chloroaldehydes and -ketones 3a-d.By 1,4-O,O-silyl rearrangement and cyanide elimination O-trimethylsilyl acyloins 4 and 9, respectively, are formed.With fluoride, 4 and 9 react to α,β-epoxy ketones 5 and 10 in high yield and with E/Z selectivities from 80:20 to >95:5.By this novel route even α,β-unsaturated epoxy ketones (10) become available.

Enantioselective Diastereospecific Synthesis of anti-α-Alkyl-β-hydroxy Esters through Cuprate Opening of Glycidic Esters

A diastereospecific chain elongation of the aldehydes 1 to anti-αalkyl-β-hydroxy esters 2 via the intermediates 4 - 7 is described.By means of the Sharpless epoxidation, 2 may be obtained with >90percent ee in either enantiomer.