211614-09-4Relevant articles and documents
Organocatalyzed Sulfa-Michael Addition of Thiophenols on Trisubstituted α-Fluoroacrylates, a Straightforward Access to Chiral Fluorinated Compounds
Huang, Xin,David, Emilie,Jubault, Philippe,Besset, Tatiana,Couve-Bonnaire, Samuel
, p. 14055 - 14067 (2020/11/20)
In this manuscript, a simple and efficient sulfa-Michael addition reaction of aryl thiols to trisubstituted α-fluoro-α,β-unsaturated esters both in racemic and, for the first time, in enantioselective version is reported. The commercially available dimer of cinchona derivatives (DHQ)2PYR was used as a catalyst. This strategy showed a great tolerance for various substrates and substituents, providing fair to excellent yields, moderate to excellent diastereoselectivities (2:1 to >99:1), and low to good enantioselectivities (2 to 87%). The reaction has been applied to the synthesis of fluorinated analogues of diltiazem and tiazesim, both therapeutic agents.
A facile and mild approach for stereoselective synthesis of α-fluoro-α,β-unsaturated esters from α-fluoro-β-keto esters via deacylation
Qian, Jinlong,Yi, Wenbin,Lv, Meifang,Cai, Chun
supporting information, p. 127 - 132 (2015/02/02)
The highly stereoselective olefination reaction of α-fluoro-β-keto esters for the synthesis of α-fluoro-α,β-unsaturated esters has been developed. The olefination combines nucleophilic addition, intramolecular nucleophilic addition, and elimination in one step, as well as provides a facile synthetic approach to α-fluoro-α,β-unsaturated esters which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.
Diethylzinc-mediated one-step stereoselective synthesis of α-fluoroacrylates from aldehydes and ketones. Two different pathways depending on the carbonyl partner
Lemonnier,Zoute,Dupas,Quirion,Jubault
experimental part, p. 4124 - 4131 (2009/09/25)
(Chemical Equation Presented) A efficient methodology allowing the one-pot stereoselective synthesis of R-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is descri
