590365-63-2Relevant 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.
