95581-18-3

Upstream product

• 41169-42-0 2,2-dimethyl-1,3-diphenylpropane-1,3-dione 
• 5659-93-8 2,2-Dimethylmalonyl chloride 
• 71-43-2 benzene 

Downstream Products

• 474882-36-5 C₃₇H₄₄O₈ 
• 832146-72-2 C₃₇H₄₄O₈ 

Relevant academic research and scientific papers

Synthesis, resolution, and applications of 3-amino-2,2-dimethyl-1,3- diphenylpropan-1-ol, a conformationally restricted 1,3-aminoalcohol

Efficient synthetic routes to both syn and anti diastereomers of a conformationally restricted 1,3-aminoalcohol were devised. Resolution of the aminoalcohols was accomplished through diastereomeric salt with R-(-)-O-acetyl mandelic acid. These aminoalcoho

Synthesis and resolution of 2,2-dimethyl-1,3-diphenyl-1,3-propanediol, a new C2-symmetric and conformationally rigid acyclic diol

Diastereomerically pure (+)- and (-)-2,2-dimethyl-1,3-diphenyl-1,3-propanediols were synthesized starting from diethyl malonate and resolved through diesters of (-)-camphanic acid and also N-carbethoxy-L-proline. The absolute configuration of the (-)-enantiomer was established by X-ray crystallography.

Diastereoselectivity in the reduction of acyclic carbonyl compounds with diisopropoxytitanium(III) tetrahydroborate

Diisopropoxytitanium(III) tetrahydroborate, ((i)PrO)2TiBH4, formed in situ in dichloromethane from diisopropoxytitanium dichloride and benzyltriethylammonium tetrahydroborate (1:2) reduces α-hydroxyketones/1,2- diketones and β-hydroxyketones/1,3-diketones to the corresponding diols with high stereoselectivity. In the case of α-hydroxyketones and 1,2-diketones, the anti isomer is the major product while reduction of β-hydroxyketones and 1,3-diketones leads to the syn isomer as the major product.

Stereoselectivity in the Hydride Reduction of Acyclic Diketones (1,2-, 1,3-, 1,4-, and 1,5-Induction)

Diketones 2, 5, 9, and 19 as well as hemiketal 22 react with lithium aluminum hydride to give mixtures of d,l- and meso-diols.The stereochemical assignment of the diols can be obtained either by direct comparison with authentic samples (1,2-diols) or by NMR differentiation of diastereotopic groups (1,3- and 1,5-diols) or by stereospecific cyclization to the sila-heterocycles 12 and 13 (1,4-diols).The 1,2- and 1,4-diketones preferably produce meso-diols, whereas 1,3- and 1,5-diketones mostly lead to d,l-isomers.These alternating stereoselectivities can be explained by a stepwise reduction generating complexes of types 24 - 27 which are attacked by excess hydride via a diastereoface differentiating mode.

Reversal of the Diastereoselectivity in the Hydride Reduction of Acyclic Diketones

3,3-Dimethyl-2,4-pentanedione (2a) is reduced to mixtures of diols 1a and 3a by a variety of hydride reagents in different solvents, the d,l-isomer 1a predominating in most cases.Addition of titanium tetrachloride reverses the diastereoselectivity favouring the formation of meso-diol 3a.All induction phenomena can be explained by a cyclic model.