99865-09-5

Upstream product

• 108-88-3 toluene 
• 99853-19-7 α-bromo phenylacetic acid allyl ester 
• 110969-20-5 bromophenylacetaldehyde allyl ethyl acetal 
• 201230-82-2 carbon monoxide 
• 1504-55-8 (E)-3-phenyl-2-methyl-2-propenol 
• 5663-20-7 5-methyl-4-phenyl-1,3-dioxane 
• 124-38-9 carbon dioxide 

Relevant academic research and scientific papers

Diastereoselective electrophilic substitution of γ-oxy-substituted benzyllithiums

Reductive lithiation of diastereoisomeric mixtures of 4-aryl-5-methyl-1,3-dioxanes occurs with epimerization at the benzylic centre. Reaction of intermediate organometals with alkyl halides or CO2 afforded 2-methyl-3-substituted-3-phenylpropan-1-ols, or the corresponding lactones, with satisfactory yields and satisfactory to high diastereoselectivities. Observed diastereoselectivities strongly depend on the substitution pattern of starting materials.

The First Stereoselective Palladium-Catalyzed Cyclocarbonylation of β,γ-Substituted Allylic Alcohols

β,γ-Substituted allylic alcohols react with CO in the presence of catalytic quantities of palladium acetate and 1,4-bis(diphenylphosphino)butane affording α,β-substituted-γ-butyrolactones in 42-85% isolated yields. The complete stereoselectivity observed

An improved synthesis of a polymer-supported distannane and its application to radical formation

A polymer-supported distannane 1 was prepared by treatment of tin halide resin with lithium naphthalenide or sodium naphthalenide in THF. The content of the polymers 1 was determined to be 0.95 to 1.13 mmol/g tin as ditin. The polymer-supported distannane reagent was successfully applied to radical cyclizations of acyclic α-haloesters to yield γ-butyrolactones.

General Synthetic Route to γ-Butyrolactones via Stereoselective Radical Cyclization by Organotin Species

A new method for the preparation of γ-butyrolactones is described in which the key step is the highly stereoselective radical cyclization of bromoacetals to 2-alkoxytetrahydrofurans in the presence of polymeric or low-molecular weight organotin species. 2-Alkoxytetrahydrofurans can be easily converted into γ-butyrolactones by Jones oxidation.