350-99-2Relevant academic research and scientific papers
Access to Constrained Fluoropseudopeptides via Ring-Closing Metathesis of Fluoroalkenes
Guérin, David,Dez, Isabelle,Gaumont, Annie-Claude,Pannecoucke, Xavier,Couve-Bonnaire, Samuel
, p. 3606 - 3609 (2016)
Bis-alkene substrates, containing one fluoroalkene and linked by an amide moiety, have been designed and synthesized to be subjected to ring-closing metathesis reactions. The substitution of fluoroalkene by a phenyl group enhanced the reactivity, and the
Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant
Zhou, Xibing,Zhang, Guoying,Huang, Renbin,Huang, Hanmin
supporting information, p. 365 - 369 (2021/01/26)
Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.
Asymmetric Synthesis of Alkyl Fluorides: Hydrogenation of Fluorinated Olefins
Ponra, Sudipta,Yang, Jianping,Kerdphon, Sutthichat,Andersson, Pher G.
supporting information, p. 9282 - 9287 (2019/05/28)
The development of new general methods for the synthesis of chiral fluorine-containing molecules is important for several scientific disciplines. We herein disclose a straightforward method for the preparation of chiral organofluorine molecules that is ba
Highly enantioselective bioreduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae
Luo, Fan,Wang, Ping,Gong, Yuefa
supporting information; experimental part, p. 1693 - 1695 (2010/04/29)
Biocatalytic reduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae was investigated in phosphate buffer solutions. Product analysis clearly showed that (S)-2-fluoro-3-arylpropanols were afforded in high yields with up to 92% ee value.
Phosphonium supported triphenylphosphine reagent: an improved access to α-fluoro-α,β-unsaturated esters
Zoute, Ludivine,Lacombe, Céline,Quirion, Jean-Charles,Charette, André B.,Jubault, Philippe
, p. 7931 - 7933 (2007/10/03)
α-Fluoro-α,β-unsaturated esters 2 were efficiently synthetized via diethylzinc-promoted Wittig reaction using a phosphonium-supported triphenylphosphine SCG-PPh3 1, which possesses similar reactivity as its parent analog triphenylphosphine. The
A facile one-pot synthesis of α-fluoro-α,β-unsaturated esters from alkoxycarbonylmethyltriphenylphosphonium bromides
Suzuki, Yumiko,Sato, Masayuki
, p. 1679 - 1681 (2007/10/03)
A convenient one-pot synthesis of α-fluoro-α, β-unsaturated esters from ethoxy- and tert- butoxycarbonylmethyltriphenylphosphonium bromide was developed. The fluorinated phosphoranes, generated in situ from alkoxycarbonylmethyltriphenylphosphonium bromides and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor), undergo a Wittig reaction with aldehydes to yield α-fluoro-α,β-unsaturated esters with (Z)-selectivity.
Tandem reduction-olefination for the stereoselective synthesis of (Z)-α-fluoro-α,β-unsaturated esters
Sano, Shigeki,Saito, Katsuyuki,Nagao, Yoshimitsu
, p. 3987 - 3990 (2007/10/03)
A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH4 in EtOH was developed. The one-pot reaction gave α-fluoro-α,β-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction predicted by the Felkin-Anh model, followed by olefination similar to the Horner-Wadsworth-Emmons reaction, has been proposed.
Low-temperature 19F NMR spectroscopy of 1-fluoro-1-lithioethenes - Stability, shifts and unexpected coupling constants
Kvicala, Jaroslav,Hrabal, Richard,Czernek, Jiri,Bartosova, Ivana,Paleta, Oldrich,Pelter, Andrew
, p. 211 - 218 (2007/10/03)
Half-lives and fluorine atom shifts of stabilized 1-fluoro-l-lithioethenes bearing hydrogen, fluorine, phenyl, and/or dimethylphenylsilyl groups in the β-positions have been determined by a low-temperature 19F NMR spectroscopy. Some 1-fluoro-1-lithioethenes displayed an exceptionally low value of the trans-3JFF coupling constant. Stereoselectivity of carbenoid formation, as well as an effect of configuration on the stability is discussed.
A ONE-POT SYNTHESIS OF UNSYMMETRICAL AND SYMMETRICAL TETRASUBSTITUTED α-FLUORO-α,β-UNSATURATED ESTERS
Tsai, Hou-Jen,Thenappan, Alagappan,Burton, Donald J.
, p. 205 - 212 (2007/10/02)
Acylation of -Li+ 1 with acid chlorides RC(O)Cl or phosgene ClC(O)Cl and subsequent reaction of the acylated phosphonate with organometallic reagents (R'M) provide unsymmetrical and symmetrical tetrasubstituted α-f
The Stereoselective Construction of (Z)-3-Aryl-2-fluoroalkenoates
Welch, John T.,Herbert, Randal W.
, p. 4782 - 4784 (2007/10/02)
The use of 2,4,6-trimethylphenyl α-silyl-α-fluoroacetate in the Peterson olefination reaction leads to the highly stereoselective formation of (Z)-3-aryl-2-fluoroalkenoates via an aldol reaction most likely proceeding through an open transition state sinc
