26927-88-8Relevant articles and documents
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
, 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.
Pd-and Cu-catalyzed stereo-and regiocontrolled decarboxylative/C-H fluoroalkenylation of heteroarenes
Rouse, Kevin,Schneider, Cdric,Couve-Bonnaire, Samuel,Pannecoucke, Xavier,Levacher, Vincent,Hoarau, Christophe
supporting information, p. 1500 - 1504 (2015/01/09)
Pd/Cu-catalyzed decarboxylative/direct C-H alkenylations of heteroarenes with α-fluoroacrylic acid is reported. This method offers step-economical and stereocontrolled access to valuable heteroarylated monofluoroalkenes as both Z and E isomers, which are known to be useful in the synthesis of fluorinated biomolecules.
Titanium mediated olefination of aldehydes with α-haloacetates: An exceptionally stereoselective and general approach to (Z)-α-haloacrylates
Augustine, John Kallikat,Bombrun, Agnes,Venkatachaliah, Srinivasa,Jothi, Anandh
, p. 8065 - 8072 (2013/12/04)
An exceptionally stereoselective and general synthesis of (Z)-α-haloacrylates, ready to undergo various synthetic transformations, has been demonstrated from α-haloacetates and aldehydes in a one-pot manner via the titanium-enolate based asymmetric aldol
Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae
Luo, Fan,Lu, Dengfu,Gong, Yuefa
experimental part, p. 101 - 107 (2012/02/04)
Biocatalytic reduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae underwent smoothly and yielded (S)-2-fluorinated alkanols with high enantioselectivities. The conversion rate was markedly depending on the configuration of alkene moiety of the substrate, the chain length of alkyl group at β position of CC bond, as well as the reaction conditions.
Synthesis of fluorinated pseudopeptides: Metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines
Pierry, Camille,Cahard, Dominique,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
experimental part, p. 2378 - 2386 (2011/05/14)
The addition reaction of organometallic reagents to N-(tert-butanesulfinyl) -α-fluoroenimines was studied. Depending of the nature of the organometallic species (Grignard reagents or zincate complexes), we were able to control the configuration of the new
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
body text, 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
Diastereocontrolled addition of organometallic reagents to S-chiral N-(tert-butanesulfinyl)-α-fluoroenimines
Pierry, Camille,Zoute, Ludivine,Jubault, Philippe,Pfund, Emmanuel,Lequeux, Thierry,Cahard, Dominique,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
scheme or table, p. 264 - 266 (2009/04/11)
Grignard and organolithium reagents efficiently react with (S)-N-(tert-butanesulfinyl)-α-fluoroenimines to provide chiral allylamines in excellent yields and with diastereomeric ratios of up to 96:4. Acidic removal of the sulfinyl group and simple functio
A convenient method for the synthesis of (Z)-α-fluoroacrylates: Lewis base-catalyzed carbonyl fluoroolefination using fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal
Michida, Makoto,Mukaiyama, Teruaki
, p. 890 - 891 (2008/12/22)
A highly useful method is established for the stereoselective synthesis of (Z)-α-fluoroacrylates from various aldehydes and fluoro(trimethylsilyl) ketene ethyl trimethylsilyl acetal in the presence of a Lewis base catalyst. The ketene acetal, easily prepared from ethyl fluoroacetate, affords α-fluoroacrylates in high yields with excellent Z stereoselectivities under mild conditions. Copyright
Efficient synthesis of fluoroalkenes via diethylzinc-promoted wittig reaction
Zoute, Ludivine,Dutheuil, Guillaume,Quirion, Jean-Charles,Jubault, Philippe,Pannecoucke, Xavier
, p. 3409 - 3418 (2008/02/11)
The synthesis of α-fluoroacrylates and α-bromo-α- fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in th
The one-pot Wittig reaction: A facile synthesis of α,β- unsaturated esters and nitriles by using nanocrystalline magnesium oxide
Choudary, Boyapati M.,Mahendar, Koosam,Kantam, M. Lakshmi,Ranganath, Kalluri V. S.,Athar, Taimur
, p. 1977 - 1985 (2007/10/03)
Nanocrystalline magnesium oxide was found to be an effective heterogeneous, solid base catalyst for the one-pot Wittig reaction to afford α,β-unsaturated esters and nitriles in excellent yields with high E-stereoselectivity in the presence of triphenylphosphine under mild conditions.
