533888-83-4

Upstream product

• 1427308-57-3 C₁₀H₆F₆O₂S 
• 546-68-9 titanium(IV) isopropylate 
• 1427308-53-9 C₁₂H₁₀F₆O₂S 
• 107-18-6 allyl alcohol 
• 29921-57-1 isopropyl 2-bromoacetate 
• 130783-02-7 3,5-bis(trifluoromethyl)thiophenol 

Downstream Products

• 533889-38-2 isopropyl 2-{[3,5-bis(trifluoromethyl)phenyl]sulfonyl}-5-methyl-2-(3-methylbut-2-enyl)hex-4-enoate 
• 533889-21-3 isopropyl 2-allyl-2-{[3,5-bis(trifluororomethyl)phenyl]sulfonyl}pent-4-enoate 
• 404825-91-8 isopropyl 2-benzyl-2-{[3,5-bis(trifluororomethyl)phenyl]sulfonyl}-3-phenylpropanoate 
• 404825-83-8 isopropyl {[3,5-bis(trifluoromethyl)phenyl]sulfonyl}acetate 

Relevant academic research and scientific papers

Mild, rapid, and inexpensive microwave-assisted synthesis of allylic and propargylic esters

A variety of allylic and propargylic esters were rapidly prepared via microwave heating of their corresponding mixed anhydride derived from pivaloyl chloride. The reaction conditions were modified to account for the sterics of the alcohol and the electronics of the carboxylic acid. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Synthesis and reactivity of π-electron-deficient (arylsulfonyl)acetates

Different π-electron-deficient (arylsulfonyl)acetates 9 were synthesized (Scheme 1, Table 1), and their behavior as soft nucleophiles in the dialkylation reaction under phase-transfer catalysis conditions was studied (Schemes 2 and 3, Tables 2 and 3). The [3,5-bis(trifluoromethyl)phenyl]sulfonyl group was shown to be the best substituent for the stereoselective synthesis of (E)-aconitates 18 via an alkylation hydro-sulfonyl-elimination integrated process under very mild phase-transfer-catalysis conditions (Scheme 5, Table 4). Sulfonylacetates 9h,i also underwent smooth Diels-Alder reactions with acyclic and cyclic dienes via in situ formation of the appropriate dienophile through a Knoevenagel condensation with paraformaldehyde (Scheme 6). Reductive desulfonylation with Zn and NH4Cl in THF was shown to be an efficient method for removal of the synthetically useful sulfonyl moiety (Scheme 7).

π-Deficient α-arylsulfonyl esters as soft nucleophiles in organic synthesis

Different π-deficient arylsulfonyl groups have been studied as candidates for the stabilization of α-sulfonyl esters. The 3,5-bis(trifluoromethyl)phenylsulfonyl group has been shown to be the best substituent for the stereoselective synthesis of E-aconitates by a dialkylation-dehydrosulfinylation integrated process under PTC conditions using K2CO3 as base.