106538-99-2

Upstream product

• 827-69-0 (E)-4-phenyl-3-penten-2-one 
• 51384-73-7 4-phenyl-3-penten-2-one 
• 98-86-2 acetophenone 
• 67-64-1 acetone 
• 1239568-87-6 (S)-4-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-2-one 
• 92511-69-8 3,5-Dimethyl-5-phenyl-4,5-dihydro-isoxazole 
• 92511-79-0 (R)-5-Methyl-5-phenyl-3-((R)-toluene-4-sulfinylmethyl)-4,5-dihydro-isoxazole 
• 92511-69-8 3,5-Dimethyl-5-phenyl-4,5-dihydro-isoxazole 

Relevant academic research and scientific papers

Trichlorosilyl triflate-mediated enantioselective directed cross-aldol reaction between ketones using a chiral phosphine oxide as an organocatalyst

Trichlorosilyl triflate-promoted directed cross-aldol reaction between ketones in the presence of a chiral phosphine oxide as an organocatalyst is described. This is the first enantioselective cross-aldol reaction between simple ketones with good enantioselectivity.

Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones

The first examples of Lewis base catalyzed enantioselective boryl conjugate additions (BCAs) that generate products containing boron-substituted quaternary carbon stereogenic centers are disclosed. Reactions are performed in the presence of 1.0-5.0 mol %

Heterogeneous versus homogeneous copper(II) catalysis in enantioselective conjugate-addition reactions of boron in water

We have developed CuII-catalyzed enantioselective conjugate-addition reactions of boron to α,β-unsaturated carbonyl compounds and α,β,γ,δ-unsaturated carbonyl compounds in water. In contrast to the previously reported CuI catalysis that required organic solvents, chiral CuII catalysis was found to proceed efficiently in water. Three catalyst systems have been exploited: cat. 1: Cu(OH)2 with chiral ligand L1; cat. 2: Cu(OH)2 and acetic acid with ligand L1; and cat. 3: Cu(OAc)2 with ligand L1. Whereas cat. 1 is a heterogeneous system, cat. 2 and cat. 3 are homogeneous systems. We tested 27 α,β-unsaturated carbonyl compounds and an α,β-unsaturated nitrile compound, including acyclic and cyclic α,β-unsaturated ketones, acyclic and cyclic β,β- disubstituted enones, acyclic and cyclic α,β-unsaturated esters (including their β,β-disubstituted forms), and acyclic α,β-unsaturated amides (including their β,β-disubstituted forms). We found that cat. 2 and cat. 3 showed high yields and enantioselectivities for almost all substrates. Notably, no catalysts that can tolerate all of these substrates with high yields and high enantioselectivities have been reported for the conjugate addition of boron. Heterogeneous cat. 1 also gave high yields and enantioselectivities with some substrates and also gave the highest TOF (43 200 h-1) for an asymmetric conjugate-addition reaction of boron. In addition, the catalyst systems were also applicable to the conjugate addition of boron to α,β,γ, δ-unsaturated carbonyl compounds, although such reactions have previously been very limited in the literature, even in organic solvents. 1,4-Addition products were obtained in high yields and enantioselectivities in the reactions of acyclic α,β,γ,δ-unsaturated carbonyl compounds with diboron 2 by using cat. 1, cat. 2, or cat. 3. On the other hand, in the reactions of cyclic α,β,γ,δ-unsaturated carbonyl compounds with compound 2, whereas 1,4-addition products were exclusively obtained by using cat. 2 or cat. 3, 1,6-addition products were exclusively produced by using cat. 1. Similar unique reactivities and selectivities were also shown in the reactions of cyclic trienones. Finally, the reaction mechanisms of these unique conjugate-addition reactions in water were investigated and we propose stereochemical models that are supported by X-ray crystallography and MS (ESI) analysis. Although the role of water has not been completely revealed, water is expected to be effective in the activation of a borylcopper(II) intermediate and a protonation event subsequent to the nucleophilic addition step, thereby leading to overwhelmingly high catalytic turnover. Copyright

Chiral copper(II)-catalyzed enantioselective boron conjugate additions to α,β-unsaturated carbonyl compounds in water

Copper pins on the boron: The enantioselective 1,4-addition of diboron to α,β-unsaturated compounds proceeds smoothly in the presence of catalytic amounts of Cu(OH)2 and chiral 2,2′-bipyridine ligand in water. A wide substrate scope of α,β-unsaturated carbonyl compounds, including acyclic, cyclic, and β,β-disubstituted enones, α,β-unsaturated esters, amides, and a nitrile, has been shown. Copyright

Copper(I)-secondary diamine complex-catalyzed enantioselective conjugate boration of linear β,β-disubstituted enones

A copper(I)-chiral secondary diamine (L-e) complex catalyzes an enantioselective conjugate boration of β,β-disubstituted enones in high yields and up to 99% ee. Product chiral tertiary organoboronates can be converted to enantiomerically enriched cross-aldol products between ketones without any racemization.

Enantiomerically Pure Sulphinyl-4,5-dihydroisoxazoles. Part 1. Stereocontrolled Synthesis of Optically Active β-Ketols and γ-Amino Alcohols

exo-Metallation of racemic 3-methyl-4,5-dihydroisoxazoles and reaction of the products with (-)-(S)-menthyl toluene-p-sulphinate afforded diastereoisomeric 3-sulphinylmethyl derivatives which can be separated and individually converted either into the cor