Z-Selective or Stereospecific Alkenylation Reaction: A Novel Synthetic Method for. ALPHA.-Fluoro-. ALPHA.,. BETA.-unsaturated Esters
M Yoshimatsu, Y Murase, A Itoh, G Tanabe…
Index: Yoshimatsu, Mitsuhiro; Murase, Yoshinori; Itoh, Akinori; Tanabe, Genzoh; Muraoka, Osamu Chemistry Letters, 2005 , vol. 34, # 7 p. 998 - 999
Full Text: HTML
Citation Number: 16
Abstract
The Z-selective formation of α-fluoro-α, β-unsaturated esters was achieved using the deselenenic acid of the syn-and/or anti-3-aryl-2-fluoro-3-hydroxy-2-organoselanylacetates 3 and 4 with trifluoromethanesulfonic acid. In contrast, the 3-alkyl-substituted propanoates 3f and 4b stereospecifically underwent alkenylation to give the (E)-or (Z)-α-fluoro-α, β- unstaurated esters 5f. We were also successful in the one-pot alkenylation reactions.
Related Articles:
Fluoro-olefins as peptidomimetic inhibitors of dipeptidyl peptidases
[Van Der Veken, Pieter; Senten, Kristel; Kertesz, Istvan; De Meester, Ingrid; Lambeir, Anne-Marie; Maes, Marie-Berthe; Scharpe, Simon; Haemers, Achiel; Augustyns, Koen Journal of Medicinal Chemistry, 2005 , vol. 48, # 6 p. 1768 - 1780]
[Pellicciari, Roberto; Natalini, Benedetto; Sadeghpour, Bahman M.; Marinozzi, Maura; Snyder, James P.; Williamson, Bobby L.; Kuethe, Jeffrey T.; Padwa, Albert Journal of the American Chemical Society, 1996 , vol. 118, # 1 p. 1 - 12]