171916-53-3Relevant academic research and scientific papers
Tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates and a synthetic approach to Cbz-Gly-Ψ[(Z)-CF{double bond, long}C]-Gly dipeptide isostere
Sano, Shigeki,Kuroda, Yoko,Saito, Katsuyuki,Ose, Yukiko,Nagao, Yoshimitsu
, p. 11881 - 11890 (2007/10/03)
(Z)-α-Fluoro-α,β-unsaturated esters (Z)-7a-f were stereoselectively prepared by a tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates 6a-f with NaBH4 in EtOH. A concise synthesis of Cbz-Gly-Ψ[(Z)-CF{double bond, long}C]-Gly (26) as a dipeptide isostere was achieved via the tandem reduction-olefination of the corresponding 2-acyl-2-fluoro-2-phosphonoacetate 20.
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.
Acylation of α-fluorophosphonoacetate derivatives using magnesium chloride-triethylamine
Kim, Dae Young,Lee, Yong Mi,Choi, Young Jae
, p. 12983 - 12990 (2007/10/03)
Acylation of α-fluorophosphonoacetate derivatives in the presence of magnesium chloride-triethylamine has been described. Acylations of triethyl α-fluorophosphonoacetate 1 and diethyl α-fluorophosphonoacetic acid 7 were proceeded under mild conditions to provide α-fluoro-β-keto esters 3 and α- fluoro-β-keto phosphonates 9, respectively, in high yields.
P-C bond cleavage of triethyl 2-fluoro-3-oxo-2-phosphonoacetates with magnesium chloride: A synthesis of α-fluoro-β-keto esters
Kim, Dae Young,Choi, Jin Seok,Rhie, Dae Yong
, p. 1097 - 1103 (2007/10/03)
P-C bond cleavage of triethyl 2-fluoro-3-oxo-2-phosphonoacetates in the presence of magnesium chloride provides a synthetic route to α-fluoro-β-keto esters.
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
Acylation of Fluorocarbethoxy-Substituted Ylids: A Simple and General Route to α-Fluoro β-Keto Esters
Thenappan, Alagappan,Burton, Donald J.
, p. 273 - 277 (2007/10/02)
(Fluorocarbethoxymethylene)tri-n-butylphosphorane (3) reacts with acid chlorides and anhydrides to form the corresponding carbon acylated phosphonium salt 4, and hydrolysis of 4 under mild basic conditions provides RCOCFHCOOEt (8) in moderate yields.The reaction is applicable to primary, secondary, tertiary, cyclic, aromatic, and ester-substituted acid chlorides.Acylation with ethyl chloroformate and ethyl chlorothioformate leads to the diesters CFH(COOEt)2 and EtSCOCFHCOOEt.Extension of this reaction sequence to perfluorinated and partially fluorinated acid chlorides did not proceed cleanly to give the expected phosphonium salts.However, the anion derived from (EtO)2P(O)CFHC(O)OEt reacts with RFCOCl to form the corresponding C-acylated phosphonates 10, and hydrolysis of 10 gives RFCOCFHCOOEt.
