133931-71-2Relevant academic research and scientific papers
Alkylation of 2-Oxy-Substituted 1-Sulfonylallyl and 1-Sulfonylvinyl Anions. New Routes to Functionalized Carbocycles and Dihydrofurans
Padwa, Albert,Bullock, William H.,Dyszlewski, Andrew D.,McCombie, S. W.,Shankar, B. B.,Ganguly, A. K.
, p. 3556 - 3564 (2007/10/02)
Alkylation of the anion derived from 2-phenoxy-3-(phenylsulfonyl)-1-propene proceeds α to the phenylsulfonyl group and affords cyclic products from 1,ω-dihalides.Reaction of the monoalkylated products, in which a suitably positioned olefinic or acetylenic unit is present, with sodium benzenesulfinate-acetic acid gives functionalized acetylcyclopentenes and cyclohexenes via C-C bond formation from the allyl cation-sulfinate ion pair.In the vinyl sulfone series, deprotonation of (E)- or (Z)-2-alkoxyvinyl phenyl sulfones rapidly affords the more stable (E)-lithio derivative, an acetaldehyde anion equivalent which reacts normally with aldehydes, ketones, alkyl halides, and epoxides.The latter process may be effected in an intramolecular fashion.Thus, (E)-(2-phenylsulfonyl)vinyl ethers of 2,3-epoxy alcohols cyclize on treatment with amide bases to afford dihydrofurans whose stereochemistry is fully defined by that of the starting epoxy alcohol.
CYCLOFUNCTIONALISATION OF EPOXYALCOHOL DERIVATIVES. 1. DELIVERY OF FUNCTIONALISED CARBON FOR STEREOSPECIFIC SYNTHESIS OF DIHYDROFURANS AND DIHYDROXYACIDS
McCombie, Stuart W.,Shankar, Bandarpalle B.,Ganguly, Ashit K.
, p. 6301 - 6304 (2007/10/02)
E-2-(Phenylsulfonyl)vinyl ethers of 2,3-epoxyalcohols are stereospecifically rearranged to 3-(phenylsulfonyl)-4-(1-hydroxyalkyl)-4,5-dihydrofurans on treatment with LDA.Oxidation of these compounds or the derived des-sulfonyl compounds provides esters or lactones which correspond to regiospecific delivery of -CO2H or -CH2CO2H to C-2, with inversion.
