724432-50-2

Upstream product

• 1422126-89-3 ((2R,4R)-4-phenoxypentane-2-yl) 4-methylbenzoate 
• 108-95-2 phenol 
• 118711-25-4 (2S,4R)-4-Phenoxy-pentan-2-ol 
• 72345-23-4 (2S,4S)-pentane-2,4-diol 
• 129098-50-6 (2R,4R)-2,4-dimethyl-1,5-dioxaspiro<5.5>undecane 
• 737758-78-0 Benzoic acid (1R,3R)-1-methyl-3-phenoxy-butyl ester 

Downstream Products

• 470475-61-7 Diazo-acetic acid (1R,3R)-1-methyl-3-phenoxy-butyl ester 
• 737764-01-1 3-Oxo-butyric acid (1R,3R)-1-methyl-3-phenoxy-butyl ester 
• 157840-11-4 (2R,4R)-2,4-pentanediol 
• 118711-25-4 (2S,4R)-4-Phenoxy-pentan-2-ol 
• 157840-12-5 (2R,4S)-2,4-pentanediol 

Relevant academic research and scientific papers

1,5-NAPHTHYRIDINE DERIVATIVE OR SALT THEREOF

A 1,5-naphthyridine derivative represented by Formula [1] (in which R1, R2, R3, R4 and R5 represent a hydrogen atom, -L-Z (in which Z represents a non-aromatic heterocyclic group or the like; and L re

Asymmetric meta-arene-alkene photocycloaddition controlled by a 2,4-pentanediol tether

Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled.

"Chiral perturbation factor" approach reveals importance of entropy term in stereocontrol of the 2,4-pentanediol-tethered reaction

The stereocontrol mechanism of the 2,4-pentanediol (PD)-tethered reaction was studied in detail using a reaction system consisting of phenyl and rhodium carbenoid moieties. Different tethers were examined to analyze the effects of the methyl groups on the PD tether. Among the reactions with these tethers, the PD tether achieves an unmeasurably high stereoselectivity in a diastereomeric ratio of >500. Another tether showing a high but measurable stereoselectivity in a ratio of 41 is mostly controlled by the entropy term. To clarify the role of the methyl groups on the chiral tethers, which are the origin of the stereocontrol, the "chiral perturbation factor" is introduced. This parameter is defined as the rate of a chiral reaction relative to that of an a chiral reference reaction. By analyzing the temperature dependence of the chiral perturbation factors for different chiral-tethered reactions, high potentials of the PD-tethered reaction in its stereocontrol are concluded to be due to the entropy term.