133577-98-7

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 1589-82-8 phenylmagnesium bromide 
• 298-18-0 (S,S)-diepoxybutane 
• 6738-06-3 phenylethynylmagnesium bromide 
• 104-53-0 3-phenyl-propionaldehyde 
• 17592-47-1 meso-1,6-diphenyl-hexa-1,5-diyne-3,4-diol 

Relevant academic research and scientific papers

Reductive self-coupling reaction of imines and aldehydes induced by strontium metal

Aromatic aldimines reacted with Sr in the presence of a catalytic amount of iodine to give self-coupling products in good yields, whereas aromatic and aliphatic aldehydes underwent a similar reaction effected by the combined use of Sr and Al(OEt)3. Copyright

Samarium diiodide-catalyzed diastereoselective pinacol couplings

(Chemical Equation Presented) A complex of samarium diiodide (Sml 2) with tetraglyme catalyzes the intermolecular pinacol coupling of aromatic or aliphatic aldehydes at loadings of 10 mol % in the presence of Me2SiCl2 and Mg. Diastereoselectivity of up to 95/5 (±/meso) has been achieved for aliphatic aldehydes and up to 19/81 (±/meso) for aromatic aldehydes. De values of up to 99% have been achieved in intramolecular pinacol coupling reactions using the Sml 2/tetraglyme/Mg/Me2SiCl2 catalytic system.

Efficient diastereoselective pinacol coupling reaction of aliphatic and aromatic aldehydes by using newly utilized low valent titanium bromide and iodide species

Reductive coupling reaction of aromatic and aliphatic aldehydes proceeded under mild conditions to give the corresponding pinacols in moderate to high yields and DL-diastereoselectivities by using combinations of either low valent titanium(II) bromide and copper or titanium(IV) iodide and copper in a mixed solvent of dichloromethane and pivalonitrile. In the case of using titanium(IV) iodide and copper, pinacols were obtained in good to high yields with moderate to high diastereoselectivities irrespective of the number of substitutuents at α-position of aliphatic aldehydes.

Efficient diastereoselective pinacol reaction of aliphatic and aromatic aldehydes by combined use of newly utilized titanium(II) bromide and copper

Newly utilized low-valent titanium reductant, titanium(II) bromide, was conveniently prepared by treating titanium(IV) bromide with hexamethyldisilane. The pinacol reaction of aromatic and aliphatic aldehydes including primary aldehydes proceeded smoothly in dichloromethane-pivalonitrile at temperatures ranging from -23 to 0 °C by the combined use of soluble titanium(II) bromide and copper to give 1,2-diols in good to high yields with good to high dl-selectivities.

Efficient method for the preparation of pinacols derived from aromatic and aliphatic ketones by using low-valent titanium reagents in dichloromethane-pivalonitrile

The reductive coupling reaction of aldehydes and ketones, including unsymmetrical aliphatic ketones, proceeded smoothly to give the corresponding pinacols in good to high yields under mild conditions by using combination of titanium(II) chloride and zinc or titanium(IV) chloride and zinc in dichloromethane-pivalonitrile. Meso-selective formation of the coupling products was observed in the cases of some aliphatic ketones. The diastereoselectivities of coupling products depend on both difference of bulkiness of 2-, and 2'-substituents of carbonyl group of the reactant, and overall steric effect around the carbonyl groups.

Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium-schiff base complexes

A new effective methodology for a highly diastereoselective pinacol coupling of aldehydes is described. The method employes 3 mol % of a complex prepared in situ from TiCl4(THF)2 and a Schiff base in acetonitrile. The catalytic cycle is realized with Me3SiCl and Mn as reducing agent. The dependence of the diastereoselectivity on the Schiff base used is reported.

Highly trans-selective intramolecular pinacol coupling of dials catalyzed by bulky Cp2TiPh

Cp2Ti(Ph)Cl in the presence of Me3SiCl and Zn provides an effective pinacol coupling catalyst for aromatic and aliphatic aldehydes.

Synthesis of chiral nonracemic diols via nucleophilic opening of (S,S)-1,2,3,4-diepoxybutane

(S,S)-1,2,3,4-diepoxybutane was synthesized from (R,R)-dimethyl tartrate. Nucleophilic opening of this diepoxybutane gave a convenient method for generating a variety of chiral nonracemic diols.