322-09-8Relevant academic research and scientific papers
Highly stereoselective radical reduction of α-Bromo-α-fluoro-β-hydroxy esters with tributyltin hydride leading to threo-α-fluoro-β-hydroxy esters
Mima, Kazuhide,Ishihara, Takashi,Kuwahata, Saki,Konno, Tsutomu,Yamanaka, Hiroki
, p. 192 - 193 (2002)
α-Bromo-α-fluoro-β-hydroxy esters, prepared as isomeric mixtures by the zinc-mediated coupling reaction of dibromofluoroacetate with aldehydes at -20°C, were successively treated with trimethylaluminium at -15°C for 0.5 h and with tributyltin hydride in the presence of a catalytic amount of triethylborane at -15°C for 4 h or at -78°C for 6 h to give preferentially the threoisomers of the corresponding α-fluoro-β-hydroxy esters in good yields.
Stereoselective Reduction of α-Fluoro-β-keto Esters by NADH and NADPH-Dependent Ketoreductases
Green, Thomas K.,Damarancha, Anil,Vanagel, Matthew,Showalter, Brandon,Kolberg, Sandra,Thompson, Alexander
supporting information, p. 4080 - 4084 (2019/06/21)
Racemic α-fluoro-β-keto esters were stereoselectively transformed to α-fluoro-β-hydroxy esters through dynamic reductive kinetic resolution (DYRKR) using commercially available NAD(P)H-dependent ketoreductases. Aromatic, alkenyl, and alkyl substrates were
A Ball-Milling-Enabled Reformatsky Reaction
Cao, Qun,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2554 - 2557 (2019/06/17)
An operationally simple one-jar one-step mechanochemical Reformatsky reaction using in situ generated organozinc intermediates under neat grinding conditions has been developed. Notable features of this reaction protocol are that it requires no solvent, no inert gases, and no pre-activation of the bulk zinc source. The developed process is demonstrated to have good substrate scope (39–82 % yield) and is effective irrespective of the initial morphology of the zinc source.
Catalyzed reformatsky reactions with ethyl bromofluoroacetate for the synthesis of α-fluoro-β-hydroxy acids
Ocampo,Dolbier, Jr.,Abboud,Zuluaga
, p. 72 - 78 (2007/10/03)
The presence of catalytic amounts of CeCl3 improves yields and simplifies procedure in the Reformatsky reactions of ethyl bromofluoroacetate with aldehydes and ketones to generate diastereomeric mixtures of α-fluoro-β-hydroxy esters, some of which can be separated by crystallization or column flash chromatography. Diastereomerically pure α-fluoro-β-hydroxy acids are obtained by mild alkaline hydrolysis of the resolved α-fluoro-β-hydroxy esters. Detailed NMR data of new α-fluoro-β-hydroxy esters and α-fluoro-β-hydroxy acids are also presented.
Ethyl α-fluoro silyl enol ether: Stereoselective synthesis and its aldol reaction with aldehydes and ketones
Huang, Xiao-Ting,Chen, Qing-Yun
, p. 3231 - 3234 (2007/10/03)
Ethyl α-fluoro silyl enol ether is stereoselectively synthesized in high yield from inexpensive chlorofluoroacetate and Mg (or Zn) in DMF (or HMPA). Lewis acid promoted aldol reaction of this enol ether with aldehydes and ketones gives α-fluoro-β-hydroxy
Oxidation of Fluoroalkyl-Substituted Carbinols by the Dess-Martin Reagent
Linderman, Russell J.,Graves, David M.
, p. 661 - 668 (2007/10/02)
The efficient oxidation of mono-, di-, tri-, and perfluoroalkyl-substituted carbinols has been accommplished by the Dess-Martin periodinane oxidant.A variety of functional groups are compatible with the oxidation procedure.Monitoring the oxidation by 19F NMR indicated that a discreet periodinane intermediate is formed during the course of the reaction.Nonnucleophilic or sterically encumbered α-thiofluoro carbinols were readily oxidized; however, a nucleophilic α-thio-substituted trifluoromethyl carbinol was not.A tert-butyl alcohol modified periodinane oxidant was ultimately employed to achieve oxidation in this example.
