80227-73-2

Upstream product

• 56539-56-1 (E)-6-Phenyl-hex-3-en-2-ol 
• 3277-89-2 phenethylmagnesium bromide 
• 123-73-9 crotonaldehyde 
• 88842-01-7 5-Phenyl-1-(phenylselenonyl)-1-penten-3-ol 

Downstream Products

• 77605-17-5 (Z)-hexa-3,5-dien-1-ylbenzene 
• 39669-95-9 (E)-hexa-3,5-dien-1-ylbenzene 
• 60550-53-0 1-phenyl-4-hexen-3-one 
• 1461649-09-1 (S,E)-1-phenylhex-4-en-3-ol 

Relevant academic research and scientific papers

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C-C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

Copper-catalyzed enantioselective 1,4-addition to α,β- unsaturated aldehydes

Figure presented The first asymmetric Cu-catalyzed conjugate addition of dialkylzinc zinc reagents to a large scope of enals in presence of phosphoramidite, SimplePhos, or (R)-BINAP ligands with enantiomeric excesses up to 90% is reported. Moreover, ACA of Grignard reagents afforded moderate to good 1,4-regioselectivities with enantioselectivities up to 90%.

Rearrangement of allylic and propargylic alcohols catalyzed by the combined use of tetrabutylammonium perrhenate(VII) and p-toluenesulfonic acid

Allylic rearrangement and/or dehydration reaction of allylic alcohols proceeds smoothly by the use of catalytic amounts of tetrabutylammonium perrhenate and p-toluenesulfonic acid hydrate. Treatment of propargylic alcohols with the catalysts at room temperature affords the rearranged products, α,β-unsaturated carbonyl compounds, while β,γ-unsaturated ketones are obtained as main products by the reaction in refluxing 1,2-dichloroethane. The application of this catalytic system is also described for the preparation of some synthetic intermediates.

Rearrangement of Allylic and Propargylic Alcohols Catalyzed by the Combined Use of Tetrabutylammonium Perrhenate(VII) and p-Toluenesulfonic Acid

Allylic rearrangement and/or dehydration of allylic alcohols proceed by the use of a catalytic amount of tetrabutylammonium perrhenate and p-toluenesulfonic acid.Treatment of propargylic alcohols with the above reagents affords the rearranged products, α,β-unsaturated carbonyl compounds.

Reactions of 3-Hydroxyvinyl Selenones with Alkoxides. Oxetane Formation and Fragmentation Reactions

3-Hydroxyvinyl phenyl selenones are prepared and their behavior as conjugate addition acceptors has been investigated.As a result, a selenonyl group has been found to activate the C=C bond for conjugate addition of nucleophiles and further to behave as an