141081-72-3

Upstream product

• 141081-71-2 (E)-5-<2-(ethoxycarbonyl)ethenyl>-2,2-dimethyl-1,3-dioxane 
• 102573-84-2 2,2-dimethyl-[1,3]dioxane-5-carbaldehyde 
• 4728-12-5 2,2-dimethyl-5-hydroxymethyl-1,3-dioxane 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 141096-58-4 5-<2-(ethoxycarbonyl)ethyl>-2,2-dimethyl-1,3-dioxane 

Downstream Products

• 141081-73-4 1-((R)-Toluene-4-sulfinylmethyl)-2,6-dioxa-bicyclo[2.2.2]octane 
• 141081-82-5 (3S,Rs)-3-<(p-tolylsulfinyl)acetoxymethyl>butan-4-olide 
• 141081-83-6 (3R,Rs)-3-<(p-tolylsulfinyl)acetoxymethyl>butan-4-olide 
• 141081-78-9 (3S,Rs)-<3,4-dihydro-6-(p-tolylsulfinyl)methyl-2H-pyran-3-yl>methyl p-toluenesulfonate 
• 141081-79-0 (3R,Rs)-<3,4-dihydro-6-(p-tolylsulfinyl)methyl-2H-pyran-3-yl>methyl p-toluenesulfonate 
• 141081-80-3 ((R)-Toluene-4-sulfinyl)-acetic acid (R)-4-oxo-2-(toluene-4-sulfonyloxymethyl)-butyl ester 
• 141081-81-4 ((R)-Toluene-4-sulfinyl)-acetic acid (S)-4-oxo-2-(toluene-4-sulfonyloxymethyl)-butyl ester 

Relevant academic research and scientific papers

Asymmetric desymmetrization of prochiral 1,3-diols via diastereoselective C-O bond fission of bicyclic acetal using a chiral sulfoxide as a chiral auxiliary

Asymmetric desymmetrization of a prochiral 1,3-diol was established by diastereoselective C-O bond fission of the chiral α-sulfinyl acetal 6. Treatment of 6 with titanium tetrachloride afforded mainly 7a via an oxonium intermediate, while with lithium diisopropylamide 7b was selectively obtained via diastereoselective β-elimination followed by an olefin isomerization.

Asymmetric Fuctionalisation of Prochiral 1,3-Diols Based on an Efficient 1,6-Chiral Induction: the Diastereoselective C-O Bond Fission in Chiral β-Arylsulfinyl Acetal via Two Types of Chelation Control

The novel asymmetric functionalisation of a prochiral 1,3-diol is accomplished by the diastereoselective C-O bond fission of the chiral β-arylsulfinyl acetal via two types of chelation controlled transition states (A and C in Scheme 4).