85363-92-4

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 37904-38-4 5-phenylpent-1-en-3-ol 
• 82772-38-1 α-(trichloromethyl)benzenepropanol 
• 182226-22-8 2-(tert-Butyl-dimethyl-silanyloxy)-4-phenyl-butyronitrile 
• 110598-66-8 (±)-2-((tert-butyldimethylsilyl)oxy)-4-phenylbutanal 
• 122-97-4 3-Phenyl-1-propanol 
• 85363-88-8 α-(dichloromethyl)benzenepropanol 

Downstream Products

• 110598-69-1 ((1R,2R)-2-Methoxy-4-phenyl-1-vinyl-butoxy)-methyl-diphenyl-silane 
• 110598-69-1 ((1R,2S)-2-Methoxy-4-phenyl-1-vinyl-butoxy)-methyl-diphenyl-silane 

Relevant academic research and scientific papers

The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction

Modified reaction conditions for improved E-selectivity of olefins in the Julia–Kocienski reaction of aldehydes having α-coordinating substituents are demonstrated. The chelating groups in aldehydes are expected to stabilize the syn-transition state with metal ions, whereas the weakly coordinating quaternary ammonium ions are devoid of all possible chelating interactions to enhance E-selectivity. A systematic investigation is presented to study the size of the neighbouring protecting groups of aldehydes and their chelation effect on E/Z-selectivity in the Julia–Kocienski reaction.

Synthesis of Polysubstituted γ-Butenolides via a Radical Pathway: Cyclization of α-Bromo Aluminium Acetals and Comparison with the Cyclization of α-Bromoesters at High Temperature

Polysubstituted butenolides were obtained in good to high yields from α-bromoesters derived from propargyl alcohols by a one-pot reaction involving the radical cyclization of α-bromo aluminium acetals, followed by the oxidation of the resulting cyclic aluminium acetals in an Oppenauer-type process and migration of the exocyclic C-C bond into the α,β-position. Comparison with the direct cyclization of α-bromoesters at high temperature and under high dilution conditions is described. Deuterium-labelling experiments allowed us to uncover "invisible" 1,5-hydrogen atom transfers (1,5-HATs) that occur during these cyclization processes, together with the consequences of the latter in the epimerization of stereogenic centres. Compared to the classical approach, the cyclization of aluminium acetals proved to be highly chemoselective and its efficiency was illustrated by the short total syntheses of optically enriched γ-butenolides isolated from Plagiomnium undulatum and from Kyrtuhrix maculans.

Improved conditions for the Kiliani-Fischer synthesis

DIBA-H reduction of O-TBDMS derivatives of cyanohydrins, followed by hydrolysis with a pH4 tartaric-buffer at low temperature produces the corresponding O-protected 2-hydroxy aldehydes in very high yields.

NOVEL SYNTHESIS OF CARBOHYDRATES USING ELECTROREDUCTION AS KEY REACTIONS

Glyceraldehyde was transformed to threose, erythrose, and erythrulose using electroreduction as key reactions.